Nomenclature of common heterocycles

All heterocycles in this course are known

by their common names. -

Type of
hd¥ typeofring-tre.tl
IUPAC names are formed from: nenberir )
↳ (d)

Heteroatom(s) as prefix + stem + suffix

↑
Nitrogen (N) = Aza Degree
of

Oxygen (O) = Oxa saturation

Sulphur (S) = Thia as unsaturated

saturated
 :&
Membered ring Nitrogen Nitrogen None Nitrogen None Nitrogen
Containing Containing
Unsaturated Saturated
Unsaturated Saturated

3-membered 0
Stem = ir Stem = ir Stem = ir Stem = ir
ring Suffix = idine Suffix = an
e.g.
No
Aziridine
suffix

Felix

How to start : if the ring is fully saturated add idine

Aza + ir + idine = aziridine
 stem for Y -
membered ring
et ⇐

t
Membered ring Nitrogen Nitrogen None Nitrogen None Nitrogen
Containing Containing
Unsaturated Saturated
Unsaturated Saturated

4-membered Stem = et Stem = et Stem = et Stem = et

ring Suffix = idine Suffix = an
NO
e.g.
suffix Azetidine
.

suffix

How to start : if the ring is fully saturated add idine

Aza + et + idine = azetidine
 I
Membered ring Nitrogen Nitrogen None Nitrogen None Nitrogen
Containing Containing
Unsaturated Saturated
Unsaturated Saturated

5-membered
ring
◦
Stem = ol Stem = ol
Suffix = idine
Stem = ol Stem = ol
Suffix = an
5- mentored e.g.
Pyrrolidine
Or to
suffix ✓
to
Azolidine
suffix
Thiophene G-

¥:|
oxide
↳ -92€ ☒ Thicke (Iupac)
Iupaenaeforpyrrok

How to start : if the ring is fully saturated add idine

Aza + ol + idine = azolidine
Furan, thiophene and pyrrole (COMMON)

The names mentioned above are common names.

The structures can be also named by IUPAC
Oxole, Thiole and Azole (IUPAC)
 SUFFIX

less ¥É

THE )
( co
-
- o
-

& qzolidine

1- here
only
-
-

less commonly used

hares
More than one heteroatom in 5-membered
ring (containing nitrogen):

Name of hetero-atoms followed by stem and

suffix mention the degree of saturation.
Heteroatoms arranged as
[O-S-N]
↑ [ lowest
highest
priority
priority

Heteroatom + stem + suffix

 O - S N -

decrea-siypri.gs
(even
in numbering)

y
\

each other Lisa )

]
becaY
in common
next to

ftnwbert
N
multiple
if
-

only
there is a
have

;e¥;Ee¥p¥ᵈ
at-0-3 ↓

p.tituents.Namead
hetero

we

i
001
0
0 0°
-

Tautomersim in imidazole and pyrazole

N NH
¥
N
H ☒É 1 .
'
'
N

☆
⑤
indicator hydrogen

N NH
N N
H ⊖

→ ÉEÉ=~→
amide-imide.CO
Numbering:
The atom mentioned first in a heterocycle
will be No. 1. Other heteroatoms are
numbered by the lowest possible number
4
4 3 4 3
N 3 N
5 2 N 2 5
5 2N O
S O
1 1 1
The provided structure can be named

8Eñ*+ñe 0×01 e

I
✗
A- Furan or thiolan
×
B- Thiophen or thiole
C- Pyrrolidine✗

g
D- Oxole
The provided structure can be named

✗ ✓
A- Furan or thiolan
0
B- Thiophen or thiole
C- Pyrrolidine 1-
D- Oxole 1-
The provided structure can be named

✗ ✗
A- Furan or thiolan
✗ ✗

B- Thiophen or thiole
saturated ✗

C- Pyrrolidine
⇐
D- Azole
 Nomenclature of the following: 0-1-1
3
y

s N
✓
H3C S
\

O
A- 5-methyl-isothiazole
-

B- 3-methyl-isothiazole
C- 2-methyl-isothiazole
D- O
4-methyl-1,2-thiazole

¥
Nomenclature of the following:

CH(CH3)2

÷ N
Cl S\

5-chloro-3-isopropyl-isothiazole
alphabetical
Nomenclature of the following:

CH(CH3)2

3N U

s
Cl
iS
2-chloro-4-isopropyl-thiazole
 Name the following:
CH(CH3)2
%•

g¥*:w
☆ ☆

;
"
N a- i
to % m

g) s
multiple CH3
's
it N
'

H
N④ indicator hydrogen
A- 2-methyl-3-isopropyl-imidazole
B- 3-methyl-2-isopropyl-imidazole
C- 5-methyl-4-isopropyl-imidazole
D- 2-methyl-3-isopropyl-pyrazole
Nomenclature of the following:
÷ N 's
g. knoledge Q
1C HE 2
occurrence
C)
rid N
•
not if
of fate ↓
-

N
H

pyrazole
A- 2-butyl-pyrazole
B- 5-butyl-pyrazole
0
C- 3-butyl-pyrazole
D- 2-butyl-imidazole
 Nomenclature of the following:

3 i

sa .

'

)
← vi. 4 A -124 tri azole
-

indicator § 1
A- 1,2,4-triazole Hydrogen

B- 1,3,4-triazole
C- 1,2,4-imidazole
?⃝
 Select the correct answer

I II III IV
a. II is the most basic compound. ✗ IV
1-

b. III is the least stable as aromatic compound

0
c. I, II, III are aromatic, but IV is non-aromatic.
d. Position 3 in I, II, and III are more favoured
for electrophilic substitution.
Classify the compound below as
aromatic, or nonaromatic. Assume \

planarity of the π network.

Cyclic ✓
C) planar ✓

Conjugated ✗

non
-
aromatic
Classify the compound below as
aromatic, or nonaromatic. Assume
planarity of the π network.
site sink
-

00
a
conjugated
> non -

planar

non -
aromatic
Classify the following compound as
aromatic, or non-aromatic.
double-double

vmcomjugabed
Electrophilic substitution on pyrrole, furan
and thiophene:
Which position is favored? Why? Explain
by equations.
Why Electrophilic substitution → 2-position?
restate
1st 2nd
At 2 structure
+ starting

At 3
less
resonance
structures
at ③
Provide the structure of the major organic
product of nitration in the reaction
below.

Nitration
%

%
#.
→
The structure of the major organic product
in the reaction below.

answer
The appropriate name of the following
compound is:

ii.
N

S NO2

a. 2-nitrothiazole
0
b. 5-nitrothiazole
c. 2-aminothiazole
d. 2-aminoisothiazole
The following structure is known as:

:
N
N
S

a)- Thiazole
b)- Isothiazole
c)- Thiadiazole
d)- Thiadiazine