B.

FUNDAMENTAL HETEROCYCLIC
SYSTEMS
SPECIALIST HETEROCYCLIC NOMENCLATURE

Rule B-l. Extension oí Hantzsch--Widman System

.ane, 1.] -Monoeyclie eompounds eontaining one or more hetero atoms in a
h the three- to ten-membered ring are named by eombining the appropriate
.rated prefix or prefixes from Tablc 1 (eliding « a " where neeessary) with a stem
The from Table 11. + The state of hydrogenation is indicated either in the stern,
ttach- as shown in Table n, or by the prefixes « dihydro- ", « tetrahydro- ", etc.,
as IS aecording to Rule B-1.2.

T ABLE 1. In decreasing order of priority

Element Valence Prefix Element Valence Prefix

Oxygen II Oxa Antimony III Stiba*
Sulfur n Thia Bismuth nI Bisma
Selenium II Selena Silieon IV Sil a
Tellurium II Tellura Germanium IV Germa
Nitrogen III Aza Tin IV Stanna
Phosphorus III Phospha* Lead IV Plumba
Arsenie III Arsa* Boron III Bora
Mercury II Mercura
l-yl
• When immediately followed by " -in " or " -inc ", " phospha- " should be replaced by
•• phosphor- ", .• arsa- " should be replaced by " arsen- " and "stiba-" should be replaced
by "antimon- n. In addition, the saturated six-rnembercd rings corresponding lo
phosphorin and arsenin are named phosphorinane and arscnanc. Further cxccptions:
borin is replaced by borinane.
TABLE U

No. 01 Rings coniaining nitrogen Rings containing no nitrogen

members Unsaturation Saturation Unsaturation Satura/ion
in the ring (a) (a)
3 -irine -iridine -irene -irane (e)
.s
4 -ete -etidine -e te -etane
5 -ole -olidine -ole -olane
6 -ine (b) (e) -in (b) -ane (d) C-\
~o/
7 -epine (e) -epin -epane
8 -ocine (e) -oein -oeane
,
9 -ornne (e) -onin -onane
10(f) -ecine (e) -ecm -eeane
(a) Corresponding to the máximum number of non-curnulative double bonds, the hetero
elements having the normal valenccs shown in Table 1.
(b) For phosphorus, arsenic, antimony and boron, sce the special provisions of Tablc l.
(e) Expressed by prefixing·" perhydro" to thc name of thc corresponding unsaturatcd
compound.
(d) Not applicab\e lo silieon, germaniurn, tin and lcad, In this case, •• perhydro- " is
prefixed to the name of the eorresponding unsaturated eompound.
(e) The syllables denoting the size- of rings eontaining 3, 4 or 7-10 mernbers are dcrived
as follows: •• ir " from tri, " et " from tezra, •• ep " from hepta, •• oc" from octa, •• on " from
nO'la, and •• ec " from deca.
(1) Rings with more than ten members are named by replacement nornenclature (cf. Rule B-4).

+ It is neeessary to elide tlie final "a" of the prefix when followed immediately by a VOIVeI,
e.g.ox(a)azole.

S3
s-r.r HETEROCYCLIC SYSTEMS

Examples: 1.51-The
2 J 4 a monocycli
l/KrCH=c,H
Example:
N~
'\H-<::H=CH
7 6 5

Oxirane Aziridine 2H-Azepine

1.2-Heterocyclic systems whose unsaturation is less than the one corre-

sponding to the maximum number of non-cumulative double bonds are
named by using the prefixes " dihydro- ", " tetrahydro- ", etc.
In the case of 4- and 5-membered rings, a special termination is used
for the structures containing one double bond, when there can be more
1.52--W}
than one non-cumulative double bond.
numbering ¡
No. of members Rings Rings
.¡ the partIy containing containing Example:
saturated rings nitrogen no nitrogen
4 -etine -etene
5 -oline -olene
Examples:
1 4 4 3
NH--CH HC===CH
I 11 I I
AsH-CH H2C, /CH2 1.53-Wl
2 3 SIH2
given to a
J
A -l,2-Azarseline· 3-Silolene numbering
1.3-Multiplicity of the same hetero atom is indicated by a prefix " di- ",
Exarnples
• tri- ", etc., placed before the appropriate "a" term (Table 1).
Example:

6H
(no!
1.3.5-Triazine (no!
l.4--If two or more kinds of" a " terms occur in the same name, their
order of citation is in order of their appearance in Table 1of Rule B-1.1. ** The numb
the sulfur
eliminates ~
the nitrog
txamples: 1
5".,s'-..!. . Iowest possi
HC l.H
ates 1,3,6-tJ
11 11
HC--N
4 3

1.2-Oxa!hiolane l,3-Thiazo!e
*As exceptions, Greek capital delta (L~), followed by superscript locant(s), is used to
denote a double bond in a compound named according to Rule B-1.2 if its name is preceded Rule B-2.
by locants for hetero atoms; and also to denote a double bond uniting componente in an
assembly of rings (cf. Examples 10 Rules A--52.1 and C-71.1) or in conjunctive names 2. ll-Tr
(cf. Rule C-55.1). list of such
'*This Rule is extended by Rule 0-1.60.
*For a rnoi

54
/'
 HETEROCYCLIC SYSTEMS B-2.11
1.51-The position of a single hetero ato m determines the numbering in
a monocyclic compound.

Example:
N
/1~
HCa 2CH
11
HC7 3~ H
I I
: corre- HC6:-.,. 'CH
ads are ~5/
C
H
is used Azocine
.e more
1.52--When the same hetero atom occurs more than once in a ring, the
numbering is chosen to give the lowest locants to the hetero atoms.

Example:

1.2,4- Triazine

1.53-When hetero atoms of different kinds are present, the locant l is

given to a hetero atom which is as high as possible in Table r. The
numbering is then chosen to give the lowest locants to the hetero atoms.
~"di-",
Examples:
6 S
6 S H C/l'NH
2 I 2 1
H C/l'N2
2 1 11 5S~ 41CH
5 N~4 ).CH 'c""
C H
H 2H,6H-l,S,2 - Di thiazine
6H-l,2,5- Thiad raz me (not: 1,3,4- Oithiazine)
(not: 2.1.4- Thiadra z me) (not: 1,3.6-0ithlazine)
(not. 1,3,6-Thiadiazlne) (not: 1,5,4- Oithiazine)
me, their
:-1.1.** The numbering must begin with The numbering has to begin with
the sulfur atom. This condition a sulfur atom. The choice of this
eliminates 2,1,4-thiadiazine. Then atom is determined by the set of
the nitrogen atoms receive the locants which can be attributed
lowest possible locant, which elimin- to the remaining hetero atoms of
ates 1,3,6-thiadiazine. any kind.
As the set 1,2,5 is lower than
1,3,4 or 1,3,6 or 1,5,4 in the usual
sense, the name is 1,5,2-dithiazine .
• is used to
~is preceded Rule B-2. Trivial and Semi-trivial Names *
ments in an
ictive names 2.11-The following trivial and semi-trivial names constitute a partial
list of such names which are retained for the compound and as a basis of
"For a more complete list see Table IV of Section D.

55
1!-2.11 HETEROCYCLlC SYSTEMS

fusion names. The names of the radicals shown are formed according
to Rule B-5.

,J
Parent Compound Radical Name
Thienyl
(9)
J
rr
S (2- shown)
(1) Throphene S
4 J

Ur
(2)
(10)
:~
(2) and (3) in earlier editions have been deleted.

(3) (11)

10 Thianthrenyl

(4)
:Ó()Ó:
6~ 4.
Thianthrene

((:o-
(2- shown)
.(12)

Furyl

~O2
o (3- shown) 03)
(5)
4 J
Furan

U
Pyranyl

(6) 60
5
o

4
HZ
J
Pyran
(2H- shown)
al
(2H- Pyr an-3-yl
o
shown)

(l4a)

6CCJ
7 1 Isobenzofuranyl
(1- shown)
(7)
5
4
J
Isobenzofuran
(Cl
(l4b)
Chromenyl
a O

rol
(2H-Chromen-3-yl shown)
(8)
'((;r
6
5 4
J
z Chromene
(2H- shown)

05)

(16)

56

/
 HETEROCYCLlC SYSTEMS B-2.! !

:i according
Paren! Compound Radical Name

:o:!:q:
Xanthenyl •
(2- shown)
/Ñame
ienyt
.hown)
'.)

(9)
X.mhene* . c():)-
Jr I
.
• Denotes excepuons LO sy sternatic numbenng.
Phenoxathiinyl

cr»-
(2-Shown)
(lO) Phenoxalhlin

2H-Pyrrotyl
(2H-Pyrrol·3-yl shown)
(11) 2H-Pyrrote
(N'jH2
Pyrrolyl
H (3- shown)
rthrenyl
.hown) s,.(', N
n 2 H
,tL-J.J3
.("2) Pyrrole
ÚL
Irridazotyl
(?- shown)
uryt H
;hown)

~
03) Imidazole

Lr
Pyrazolyl
ranyl .~' (l- shown)
-3-yt shown)
O
" 'CH2
(14)
5

4
(jJ 1 N
3
2
Pyrazole
(N'II
I

J-
lsothiazotyt
s
SrLJt
a
(3- shown)
izofuranyl (I4a) lsothiazote
shown) 4 3

:eL Isoxazotyl
(3- shown)
ornenyl
en-3-yl sbown)
(I4b) lsoxazote

a
0 2

60~, Pyridyl
0- shown)
(15)
S
2
3
Pyridlne
O-
6¡(~~2
(16) Pyrazine
sllNJ3
,4
57
B-2.11 HETEROCYCLIC SYSTEMS

Parent Compound Radical Name

60 NJ
Pyrimidinyl
(2- shown)
2
(17)
5

N
,
Pyrimidine

G~ (2S)
:l
60
Pyridazrnyt
2 (3- shown)
(lB)
5 3
Pyridazine

Ct (26)
:l
en-
Indolizinyl

6 '
8 1
(2- shown)
(l9) 7~2 Indolizine

5
3
(27)
J
7 1 IsoindolyL
(2- shown)
(20) 6(OH
5
,
3
Isoindole
(C1- (28)
;l
3H-Indolyl

(21) '(Jó
5 3CH2 3H-Indole
(3H-Indol-2- yl shown)

((<t-
4

H Indolyl
(1- shown)
CH2
(29)
:l
(22)
'(:6'
5 )
lndole

(ú
I

Indazolyl
(30)
:l
7 N
H
(1H-lndazol-3- yl shown)

(23) 5(l3J lH-lndazole

CD-
H
5
4
3
(31)
:l
H Purinyl*

(24) 'Njeon
N 9N
2~'
Purine*
(8- shown)

N:JLir
H

(32)
3
~N. N .- -- :C
• Denotes exceptions to systematic numbering.
 HETEROCYCLIC SYSTEMS B-2.11

le
,yl Paren! Compound Radical Name
In)

aGOz
9 1 4H-Quinolizinyl

I
~

nyl
m)
(25)
7~ ,C
6
5N
H2
3
4H-Oulnollzlne

ro-2
(4H-Ouinolizin-2-yl

H
shown)

,
'l
L (26) 7(02
6
8

5 4
3
ls oquinotine

CO-
lsoqumolyí
(3- shown)

\yl
Nn)

)- Quinoly1

(27)
:0): 4
Oumolme
(2- shown)

00-
yl
vo)
>-"'N- Phthalazinyl

7CC~2
8 1
(1- shown)
d
oó
(28) Phlhalazine
6 N3
5 4
.Iyl
shown)

7002
N't- 8 Naphthyridinyl
(1,B-Naphthyridin-2-yl shown)

00-
~CH2 Naphthyridine
(29)
6 3 0,8- shown)
I 5 4
m)
I

) Quinoxalinyl

yl
(30)
;aJ:5 ~
Ouinoxaline
(2- shown)

or::r
-yl shown)
H
Ouinazolinyl
N'N
-.JL (31)
'00
6
5 4
3
N
Ouinazoline
(2- shown)

0Cr
1*
Nn)
Cinnolinyl

10:;y
H 8 N
N" (3- shown)

-N
Ir (32)
6
5 4
3
Cinnoline

Cú-
B-2·LI HETEROCYCLIC SYSTEMS

Parent Compound Radical Name

8 Pleridinyl
N (2- shown)
lO
7e ))
(Jet
(33)
6

~ ,
JN
Pteridine (40)
90
8 N
N 7
9 4aH-Carbazolyl *

(34)
:CLú: ~ ,
4aH-Carbazole*
(4aH-Carbazol-2-yl

O:-~
shown)

(41)
:0
9

H Carbazolyl*
(2-shown)
9
(35)
'(éó'
6
s 4
J
Carbaz,lle*
()LO-
H

(42)
:0 6

H ¡3-Carbolinyl

:CCCJ,
(¡3-Carbolin-3-yl shown)
H
(6)
'" -Carboline
(Seepage 466,
s • paragraph 2)
~
--
9
09'
2
Phenanthridinyl

:0
cO
(3- shown)
9 10'. 4 (44)
(37) Phenanlhrld ine

a 5 N
7 6

'ceo'
e 9 1 Acridinyl*

(38)
6
I

H
4
J
Acridine'"

coo- (2- shown)

Perimidinyl (46)
SN
J
.2)6,
1 C- J (2- shown)

(39) Perurudme HNAN

8.
6
5

• Denotes exceptions ro systernatic numbering.

66 (47)
:0
9
6

60
 HETEROCYCLIC SYSTEMS B--2.11

-Parent Compound Radical Name

l Name
?henanlhrolinyl
2

o(9
( 1.7- Phenanlhrolin -3- yl shown )
f iny l N3
own)
10 4 Phenanlhroline
(40) 9
0,7- shown)

6 5
~ 6

:o-
vazolyl* Phenazinyl

:cóo'
,1-2-yl shown)
(1- shown)

a:JÓ
(1.1) Phenazme

6 5 4

.zolyl*
iown)
-! Phenarsazinyl

tr :d~lÓ:
(2- shown)
(1.2) Pbenar sazme

6 5 4

sr botiny I

:v
n-3- yl shown)

Phenolhiazinyl

e-
1thridinyl (2- shown)
;hown)

OC::o-
(1.4) PhenOlhiazine
H

:o-
dinyl*
;hown)

Furazanyl
(3- shown)
rirnidmyl (46) Furazan N'/o....N
shown) (See page 466,

AN paragraph 2) 11 11

:ó (47) Phenoxazine
Phenoxazinyl
(2- shown)
H

(())

61
 B-2.12. HETEROCYCLIC SYSTEMS

B-l.12-The following trivial and semi-trivial names are retained but

are not recommended for use in fusion names. The names of the radicals Pó
shown are formed according to Rule B-5. H
/N"
Parent Compound Radical Name HzC5 I 1
(8)
Isochromanyl ~
8 H¡ (3· shown)
C

(1) 7(r'iO
6
5 H¡
3 '
C/CHz
Isochroman
((~~ ~H- H2~6
/N,
H

I :
C/ (9)
H2 H (5 , :
2 "C ....
Chromanyl

-oc
Hz
8 O (7- shown)

(2) 7(r121HI Chroman O

6 4)CHz "CH, 2
H
S C CH ¿N,
H¡ C/ 2 H C6 1
H2 2,
(10)
H2C~4
N/
Pyrrolidinyl H
H
/N, (2- shown)
H2CS I zCHz H
(3) Pyrrolidine N
HzC--CHz H c-' 'CH- 7
" 3' Zl I

H
H2C--CH¡

Pyrrolinyl
(2- Pyrrol in-3- yl*shown)
(11)
:0
H s 12 Pyrroline H /
(4) z1 N 7
~ 3

:0
H2C4 (2- shown*) 2
HC.=l
1
H2C (12)

4
Imidazolidinyl
H
N (2- shown)
H¡C'S'1'2CHz H
(5) I I Imidazolidine N N
HzC~NH H C/ 'CH-
zl 1 HzC-fí b
HzC--NH
Imidazolinyl
(13) I 71
H H CS sC
(2-lmidazolin-4- yl *shown) 2,,1
H2C/N"
S 1 zCH H
C
t-'
, 11 Imidazoline
(6) N 4
HzCL...lN (2- shown*l H C/ 'CH
2, 11
-HC-N e
(14)
Hp('
,
Pyrazolidinyl H2C~,
H (2- shown) ~
/N,
H2Cs 1 zNH H
~
(i) I 1 Pyrazolidine
H2CL...lCHz H C/N'N_
zl I
HzC-'-CH2
• The " 2- " denotes the position of the double bond.

62

-
 HETEROCYCLIC SYSTEMS B-2.12

are retained but Compound Radical Name

Par erit
les of the radicals Pyrazolinyl
(3-Pyrazolin-2 - yl*shown)
H
Pyrazoline N
lical Name (8) H C,.. 'N-
(3- shown*)
lsochromanyl 2b=::J
(3- shown)
Piperidyl t
~~ (2- shown)

(( C"""
~H-
(9) ,
H
......
N,C
H¡C6 1 2 H2
I Piperidine H C"'" 'CH-
H
N

H2 C5 4 lCH¡ 21 I
H2 'c......
Chromanyl H2C CHz
.....
H2 'c
(7- shown) H2
O-"'CH Piper azmy 1
-(( I 2 H (1- shown)
CH2 N, I
C""" H2C-( 1 2CH¡
p, perazine N
H2 (lO) I I H¡C""" 'CH¡
H2CS4 lCH¡
'N""" I I
H H2C ,CH1
Pyrrolidinyl 'N'
H
(2- shown)
H lndolinyl
N (1- shov.n )
H
H C'"
2, -"'CH-
1 7 N
2
I
H2C--CH2 (11 ) 6 (C]CH
lrrdotine
I
(X
J N'CH
S CH¡ I 2
Pyrrolinyl 4 -CH2
,rrol in-3- yl *shown)
soindotiny'

'éx\~
í

H
N (1- shown)
H C"""'f1
21~ H,C"""
(12) 2NH lsoindoline
H2C
5"
4
't/
H¡ (('C~NH
lmidazolidinyl
(2- shown) H¡
H Guinuclid Inyl
N N (2- shown)
H C'" 'CH-
2, I H c~l'tcH2 N
H2C--NH (13) 2\ 7TH2 \ Guinuclidine H2C/¿~CIH-
. lmidazolinyl
dazolin -4- yl *shown)
sCH
H2C~I/CH2 H2C
I tH .
1 :-'CH2
C "C'"
H H H
4
.....N'CH
C Morpholinyl f
H21 11
(3- shown)
-HC-N
(14) I °
H¡C't' )CH¡
I Morpholine H C O'CH
z 2
Pyrazolidinyl H2C54 lCH2
'N""" I 1
(2- shown) H2C, /CH-
H
H N
N H
H C"'" 'N-
21 1 • The •• 3- " denotes t~e !X?si.tionof the double bond.
H2C"--CH2
t For l-Piperidyl use piperidino ".;
t For 4-Morpholinyl use morpholmo.
te bond.
B-3.1 HETEROCYCLIC SYSTEMS

Rule B-3. Fused Heterocyclic Systems (e) A co

any kind.
3.1-" Ortho-fused" and "ortho- and peri-fused" ring compounds
containing hetero atoms are named according to the fusion principle Example
described in Rule A-21 for hydrocarbons. The components are named
according to Rules A-21, B-l and B-2. When the name of a component
in a fusion name contains locants (numerals or lettcrs) that do not apply
also to the numbering of the fused system, these locants are placed in square
brackets (as are also the locants for fusion positions required by Rule A-21.5).
The base component should be a heterocyclic system. If there is a choice,
the base component should be, by order of preference :
(j) A eo
(a) A nitrogen-containing component.
Example
Example: 2

ó&
N
3

'o
9 4

8 / S
lH-P"j
7 6 not lH-
Benz[h]isoquinoline
no! Pyridc.[3.1,- al riaph tho ie ne (g) A cc
(b) A component containing a heteroatom (in the absence of nitrogen) as listed in T:
high as possible in Table 1.
Example
Example: 6

5¡(SY?'ñ 2

4~3

Thieno[2,3- b]furan
no! Furo [2,3- b] thiophene

(e) A component containing the greatest number of rings.

Example: (h) If tl
the same 1
that one '"

. Examph

7H-Pyraz,no[2,3 - e] carbazole
not 7H-lndolo[3,2- r]qu,noxal,ne

(d) A component containing the largest possible individual ring.

Example: 7 O
6~Y'2~H2 3.2-If
5l(~~3 the comp'
O hetero ato
4

2H-Furo [3,2- bJ pyran • In this e

not 2H-Pyrano [3,2- bJ furan of sulfur atoi

64
 HETEROCYCLIC SYSTEMS B-3.2

(e) A component containing the greatest number of hetero atoms of

any kínd.
~ compounds
.ion principle Example:
ts are named 7N~~~;
'a component 6¿:....¡~3
do not apply e 4
iced in square H2
Rule A-21.S). 5H- Pyrido [2.3- d]-o-oxazlne
re is a choice, no! o-Oxazino[4,5-b] pyridine

(J) A component containing the greatest variety of hetero atoms.

Examples:
.6
N S
5(''1(T~
4HN-WN

lH-Pyrazolo[4,3-d] oxazote 4H -Imidazo [4,5 -d] th iazote

not 'lH -Oxazolo [5,4 - cJ pyrazote not 4H- Thlazolo[4,5-d] irrudazole

(g) A component containing the greatest number of hetero atoms first

listed in Table 1.
of nitrogen) as
Example:

Selenazoto [5.4-f] benzothiazote ~: .\

no! Thiazoto [5.4 -f] benzosetenazote

(h) If there bis a chdoic~bdetwehencomponenths of the sthamebsizecontaining .t

the same nuro er an km o f etero atoms e oose as e ase component
that one with the lower numbers for the hetero atoros before fusiono

Example:

7¡Jy~~2
6N~3
5

al i ing. Pyrazmo l2,3-d) pyridazine

3.2-If a position of fusion is occupied by a hetero atom, the names of

the component rings to be fused are so chosen as both to contain the
hetero atoro.
• In this example the hetero atom first listed in Table I is sulfur and the greatest number
of sulfur atoms in a ring is one.
8-3.4 HETEROCYCLlC SYSTEMS

Example: are indicar

6r(~~n2 numbers b
5LN~3 thus:

lmidazo [2.1-b] thiazole

3.3--The following contracted fusion prefixes may be used: furo,

:c
imidazo, isoquino, pyrido, pyrimido, quino and thieno. Iv

Examples:

ca
6
l

9 3 7

: 6
~
Pyr
(

Furo [3.4-c]cinnoline 4H-Pyrido[2,J-c] carbazole

3.4-In peripheral numbering of the complete fused systems, the ring

system is oriented and numbered according to the principIes of Rule A-22.
When there is a choice of orientations, it is made in the following sequence
in order to:
(a) Give low numbers to hetero atoms, thus:
(d) Giv.

:6:):
6 S
6N9)2 SCJL!2'CH I 2
S~3 HN 3 O
4 4 4

Benzo[blfuran Cyc !openta [b J pyran 4H-[ 1.3]üxalhiolo[5,4-b]pyrrole

(note; 1,3,4 Iower than 1,3,6 )
(e) The
(b) Give low numbers to hetero atoms in order of Table 1, thus: all hetero
hetero ato
6
previous n
5r('Sy9 n2

4~3 3.5-As
a hetero r
Thieno [2,3-b] furan
of the het
(e) Allow carbon atoms common to two or more rings to follow the componen
lowest possible numbers (see Rules A-22.2 and A-22.3). [A hetero atom B-3.4 (a),
common to two rings is numbered according to Rule B-3.4(e)], thus: for compc

8 Exampl
7
6rsW"'I~2
N

not or
7¡(Ny~)2
5N ==l-.4)3 &--N 4 3
N 5 'N

Imidazo[ 1.2-b][ 1.2.4]triazine*

In a compound name for a fusion prefix (i.e., when more than one pair
of square brackets is required), the points of fusion in the compound prefix
*ln Hantzsch -Widman names the locants are inseparable from the name.

66
 ·1 .
HETEROCYCLIC SYSTEMS B-3.5
are indicated by the use of unprimed and primed nurnbers, the unprimed
nurnbers bcing assigned to the ring attached directly to the base component,
thus:

ay be used: furo,

90- .;~N:t~n~ 1
9,
I'J 11 I 12
).

4
3

H
8

7
6.
N
6
5"
N
5
4.
4
3
not
:6-:::(Xj:
7 6 5 4

Pyrido fr. 2': 1,2Jimidazo-

5 [4,5- bJ quinoxalme
6 or

-] carbazote

10 11 12
cd systems, the ring
icíples of Rule A-22.
le following sequence
or
:Cr":LÚ:
7 N
6
5
4

(d) Givc hydrogen atoms lowest numbers possible, thus:

6 S

:L! Z-CH2 (')[O'9 H2

3 I
O H °
4H·1 ,3 - Dioxolo [4,5-d ] imidazole
athiolo[S ,4-b [pyrrole
lower than 1.3.61
(e) Thc ring is numbered as for hydrocarbons but numbers are given to
Table 1, thus: all hetero atoms even when 'common to two or more rings. Interior
hetero atoms are numbered last following the shortest path from the highest
previous number,

3.5-As cxceptions, two-ring systems in which a benzene ring is fused to

a hetero ring may be named by prefixing numbers indicating the positions
of the hetero atoms to benzo followed by the name of the heterocyclic
component. umbering is assigned by the principIes set forth in. Rule
e rings to follow the
B-3.4 (a), (b), and (d). The names provided by this rule may also be used
:.3). [A hetero atom
for components of more complex fused systerns.
B-3.4(e)], thus:
8 Examples:
7cNy~)2
ro
r
6 N
5 'N
4 3
8
6 5 4
J
'2
((~ H2
3 - Benzoxepin t. H - 3,1 - Benzoxazine
n more than one pair
(not Benz [dloxepin) (not t.H- Benz[d]C1,3]oxazine)
the compound prefix
1 (he name.

67
B--4.1 HETEROCYCLIC SYSTEMS

H
heterocycli
e2 principies;
N2) (a) Whe
J
lH-PyrrOlO[1,2- b][ 2 benzozepine number of
(not lH - Benzo[ e]pyrrolo[1,2- a]ozepine) use of hydi
state of hyc
Rule B-4. Replacement Nomenclature (also known as •• a " Exarnple
Nomenclature)*
4.1-Names ofmonocyclic hetero compounds may be formed by prefixing
•• a" terms (see Table 1 of Rule B-1.1), preceded by their locants, to the
name of the corresponding hydrocarbon]. Numbering is assigned so as to
give locant I to the hetero atom listed earlier in Table 1, next to hetero atoms
as a complete' set, and then to hetero atoms in order of Table 1. I f a further
choice is possible, numbering is assigned according to Rule C-O.IS.

Examples:
(b) Whel
H2
in the skel
S(]2
4
S'

3
Sila-2,4 -cyclopentadiene hetero ator
compound
of conjugar.
is named ii
cumulative
Sila -1, 3 -cyclopentadiene
heterocyclic
the " a " te
H

6r(Y~2 Silabenzene
SV 4
3

7~~'

1- Thia-l.- aza -2,6-disilacyclohexane

6~S'
5 4

4.2-Fused heterocyclic systems may t-e named by prefixing " a " terms
preceded by their locants, to the name of the corresponding hydrocarbon.
The numbering of the corresponding hydrocarbon is retained, irrespective
of the position of the hetero atoms; where there is a choice, low numbers
are assigned in the following order: first to hetero atoms as a complete set, * Isolated d
next to hetero atoms in order of Table 1, and then to multiple bonds in the
*The Stelzner Method is abandoned.
[The "corresponding hydrocarbon" is obtained from the heterocyclic compound by

formally
valence
replacing each hetero atom with >CH., /~CH, or
2, 3 or 4 of the hetero atom replaced.
-L, in accord with the

68
 HETEROCYCLIC SYSTEMS B-4.2
heterocyclic compouncl according to the priuciples of Rule A·-ll.3. These
principies are applied in one of two ways, as follows :

(a) When the corresponding hydrocarbon does not contain the maximum
number of non-cumulaLive double bonds and can be namccl without the
use of hydro prefixes, as for indan, then the hydrocarbon is narned in that
state 01' hydrogenation.
as "a" Exarnple :

)y prefixing
ants, to the H
red so as to
hetero atoms
. lf a further
15.
©C6 7
N5 4
1 21'5
35

2,3-0 ithia-1,5-di azain dan

(b) When the two conditions of paragraph (a) are not Iulfillcd, positions
in the skeleton of the corrcsponding hydrocarLon that are occupied by
~nladlene hetero atoms are denoted by " a" prefixes, anI the parcnt heterocyclic
compound is considered to be that which conta .ns the maximum number
of conjugated 01' isolated* double bonds, but the r orresponding hydrocarbon
is named in the form in which it contains the maxirnurn number of 11011-
curnulative double bonds. Hydrogen additional to that present in the parcnt
~nladiene
heterocyclic compound is named by hydro prefixcs and/or as H in front of
the " a " terms.

7(X/liCH
6
8 S

•
·1 z
JS 4H ·1.3· Dilhianaphthalene
5 C""
H¡

:lohexane 1.'- ·Dithiana;;hthalene

" a " terms 2,L..6 -Trtthia ·3a.7a· diazaindene

,ydrocarbon.
irrespective
ow numbers
:omplete set, • Isolated double bonds are those which are neither conjugated nor cumulative as in
bonds in the

compound by

ccord wi th the

69
B-4.2 HETEROCYCLIC SYSTEMS

Examp

69
~~ w

• 3 lH-2-0xapyrene
7 4
6 5

7
6 09.
5

8 N9
3

10
1

2
N

2;1,9-Tfiazaphenanthrene

5.13-)
4.3-In fusion names, the " a " terms precede the completed name of removal ,
the parent hydrocarbon. Prefixes denoting ordinary substitution precede are narne
the " a " terms.
Example: Examp

3,4-Dimethy\ - 5 -azabenz [a] anttvacene

5.21-'
Rule B-5. Radicals radical n
5.11-UnivaIent radicals derived from heterocyclic compounds by carbon al
removal of hydrogen from a ring are in principIe named by adding " yl " or in par1
to the names ofthe parent compounds (with elision offinal "e", ifpresent).
ExampIes: Examp
IndoIyI from indole
PyrroIinyI from pyrroline
Triazolyl from triazoIe
Triazinyl from triazine
(For further examples see Rule B-2.11.)
The following exceptions are retained: furyl, pyridyI, piperidyl, quinolyl,
isoquinolyl and thienyl (from thiophene) (see also RuIe B-2.12). Also re-
tained are furfuryl (for 2-furylmethyl), furfurylidene (for 2-furylmethylene),
furfurylidyne (for 2-furylmethylidyne), thenyl (for thienylmethyl), thenyl- Rule B-I
idene (for thienylmethylene) and thenylidyne (for thienylmethylidyne). 6.1-A
As exceptions, the names " piperidino " and " morpholino " are preferred containin
to " l-piperidyI " and " 4-morpholinyl ". rules by
5.12-Bivalent radicals derived from univalent heterocyclic radicals •• thionia
whose names end in "-yl" by removal of one hydrogen atom from the Cationic
atom with the free valence are named by adding " -idene " to the name of cationic ;
the corresponding univalent radical. etc. (cf. '

70
r

l-IETEROCYCLIC SYSTEMS B-6.1

Example:

50'2
5
o
C
=
3
H
f16~"2n
4 l1z~JlJ
2H·Pyran-2-ylidene 11
t. (IH)-Pyridyl idene
or l.t. - Dihydro-t. - pyridylidene
.nthrene

5.13-Multivalent radicals derived from heterocyclic compounds by

d name of removal of two or more hydrogen atoms from different atoms in the ring
m precede are named by adding " -diyl ", " -triyl ", etc., to the name of the ring system.

Example:

'w
5
5
, ~;

2.4-Quinolinediyl
a

5.21- The use of " a" terrns (Rule B-4) does not affect the formation of
radical names. Such names are strictly analogous to those of the hydro-
oounds by carbon analogs except that the " a ti terrns establish enumeration in whole
ding " yl ti or in parto
if present).

Examples:

,cy?89 1 2
5 4 3

5 Il

-l, quinolyl, 1.3-Dioxa· 4 -cyclohexyl 1,IO-Di¡¡za-4- anlhryl

l. Also re-
nethylene),
yl), thenyl- Rule B-6. Cationic Hetero Atoms
Iidyne) . 6.1-According to the "a" nomenclature, heterocyclic compounds
re preferred containing cationic hetero atoms are named in conformity with the preceding
rules by replacing "oxa- ", "thia- ", "aza- ", etc., by "oxonia- ",
lic radicals " thionia- ", " azonia- ", etc., the anion being designated in the usual way.
n from the Cationic hetero atoms follow immediately after the corresponding non-
he name of cationic atoms: oxonia follows oxa, thionia follows thia, azonia follows aza,
etc. (cf. Table 1 of Rule B-l.l). (ef. Rule C-82 and C-83).

71
B-IO.I HETEROCYCLIC SPIRO COMPOUNDS

Examples: Examples: .

I'N

:W), l-Oxoniaanlhracene chloride 4

2'U
5 10 4

:0 7

6~03
7~
4a -Azoniaanlhracene chloride 3,3'-Spir

5 lO + 4
Rule B-11. C
11.1-Hetero+
the following cr
numbers as low
cr 1-Thioniabicyclo[2.2.1] heplane chloride ponent systems;
components of
decided accordi
clarity in compl
Examples:
l-Melhyl-l-oxoniacyclohexane chloride

r\;,~
HETEROCYCLIC SPIRO COMPOUNDS 4LKJ
5 6 3
Rule B-IO. Compounds: Method 1

'
Cyclohexanespiro
IO.I-Heterocyc1ic spiro compounds contammg single-ring units only hydrofurar
may be named by prefixing " a " terms (see Table I, Rule B-1.I) to the
H
names of the spiro hydrocarbons formed according to Rules A-41.I, A-41.2,
A-41.3 and A-41.6. The numbering of the spiro hydrocarbon is retained
and the hetero atoms as in Rule B-4 are given as low numbers as
are consistent with the fixed numbering of the ring. When there is a
choice, hetero atoms are given lower numbers than double bonds.

Examples:
6

7
& 5

8
3' 4'

N'
H1

9¿ I~ol 23
1,2,3,4-Tetrahydr
6q 72 spiro-4'-p
8
OCJ
9 lO 4
S
)
14 "'-/
7 5 4
2 cr
Rule B-12.
12.I-Radic
I

1-0xaspiro [4. 5]decane 6,8- Diazon iadispiro [5.1.6.2] hexadecane Rule B-IO.I al
dichloride and B-5.2l.
are named by
IO.2-If at least one component of a mono- or poly-spiro compound is a compound (wi
fused polycyc1ic system, the spiro compound is named according to Rule numbering of
A-41.4 or A-41.7, giving the spiro atom as low a number as possible attachment are
consistent with the fixed numberings of the component systems. ing of the hete

72 :-O.O.\.-D
 HETEROCYCLIC SPIRO COMPOUNDS E-12.1
Examples:
7'
6'

S'
ride

3,3' -Spirobi[3H-indole] Spi ro [pip er idine - 4,9'- xanlhene]

"Ioride

Rule B-II. Compounds: Method 2

l1.I-Heterocyclic spiro compounds are named according to Rule A-42,
the following criteria being applied where necessary: (el) spiro atoms have
numbers as low as consistent with the numbering of the individual corn-
itane chloride ponent systems; (b) heterocyclic components have priority over homocyclic
components of the same size; (e) priority of heterocyclic components is
decided according to Rule B-3. Parentheses are used where neccssary for
clarity in complex expressions.
Examples:
eane chloride

)8
K,~ll5' 3'

4'Q()S
Z' O 6

4~
5 6 3 4' 5' .6' 3 4

~ '
Cyclohexanespiro -2~(tetra- Tetrahydropyron-2-spiro- 3,3'-Spirobl (3H- ind:::I')
e-ring units only hydrofuran) cyclohexane
ule B-l.I) to the
:S A-4l.1, A-4l.2, H

carbon is retained
low numbers as
When there is a
.e bonds.
6

7
c8
5

8
3' 4'

N
H1
6'

1.2,3,4-Tetrahydroquinoline -4-
S'

Hexahydroazepinium -1-spiro-I'-lmidazolidine-3'-
spiro-4'- piperidine spiro-l"- piper idiniurn dibrornide

Rule B-12. Radicals

12.I-Radicals derived from heterocyclic spiro compounds named by
hexadecane Rule B-IO.I are named aecording to the principles set forth in Rules A-U
and B-S.21. Radicals derived from other heterocyclic spiro compounds
are named by adding "-yl", "-diyl", etc., to the name of the spiro
piro compound is a compound (with elision of final" e ", if present, before a vowel). The
according to Rule numbering of the spiro compound is retained and the point or points of
umber as possible attachment are given numbers as low as is consistent with any fixed number-
ystems. ing of the heterocyclic spiro compound.

:-"0.('.-0 73
B-12.1 HETEROCYCLIC RING ASSEMBLIES

É,<amples:

1-Oxaspiro[4.5Jdec-2-yl
(cf. Rule 8-10.1)
or Cyclohexanespiro-2~(tetrahydrofuran)-5'-yl
(cf. Rule 8-11.1)

Rule B-14.
14.1-Bri
of Rules A-
Rule B-4.2
Spiro [benzofuran- 2 (31-/), 1~cyclohexan]-'~yl Examples

6' l' H2
/
H2CS'
CH -S Cro
2 "-13
2'C2,
s
87
6

"
CH-CH
I
e 3'/
2

Spiro[naphthalene -2 (3Hl. 2'-thian]-4' -yl

HETEROCYCLIC RING ASSEMBLIES

Rule B-13
13.1-Assemblies of two or more identical heterocyclic systems are named
by placing the prefix " bi-", " ter-", "quater-", etc., before the name
of the heterocyclic system or radical. The numbering of the assembly is
that of the corresponding heterocyclic systems, one component being as-
signed unprimed and the otbers primed, doubly primed, etc., numbers.
The points of attachment are indicated by appropriate locants before the
name. Other structural features are described as recorded for hydrocarbon
ring assemblies in Rules A-52.1 (double bond between two components), Rule B-15.
A-52.3 (substituents), A-53.3 (hydrogenation), A-54.1 (numerical prefixes), B-15.1-.
and A-55.1 and A-56.1 (radicals), insofar as fixed numbering of the " ortho- and
heterocyclic system allows. one or mor-
peri-fused "
Examples: exemplified
bridge conté
o
r('(-ih
O
Áll';h
terminal at<
lk..1tV ~ a prefix beii
the formula
2,3'-Bifuran same order
or 2, 3'- Bifuryl are cited in

74
~15.2 BRIDGED HETEROC:YCLIC SYSTEMS

Azimino -N =N-NH-
Azo -N=N-
Bümino -NH-NH-
Epidioxy -0-0-
Epidithio -S-S- N
Epithio -S-
Epithioximino -S-O-NH-
Epoxy (see also Rule C-212.2) -0-
Epoxyimino -O-NH-
Epoxynitrilo -O-N =
Epoxythio -O-S-
Epoxythioxy -O-S-O-
Furano (usual1y3, 4-) -C4H20-
Imino (see also Rule C-815.2) -NH-
Nitrilo -N=
15.2-Systems described in Rule B-15.1 are numbered according to the
principies set forth in Rules A-34.1 and A-34.2 for compounds containing
hydrocarbon bridges. In the name of the complete compound, the name
of the bridge is preceded by two locants, that for the unit cited first in a
composite bridge preceding that for the other end of the bridge. Radicals
derived from the polycyc1icsystemsdescribed in Rule B-15.1 are formed by
the principIes set forth in Rule B-5.
H

H
1.4 - Dihydro-1,4 -epoxynaphthalene

7
6

Perhydro-l, 4-epoxy-4a,Ba-( melhanoxy-

m el hano)n aphthalene

6~7 9' '-.2

0- -CH2
5 3
4

Perhydro- 5, 3-( epoxymelhano) benzofuran

6~7
8 ~
O2
-o~
5 3
4

Perhydro - 3, 5 -(epoxymethano)benzofuran

76