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N
S
Prepared by O
Nomenclature of heterocyclic compounds
1
I- Common Nomenclature
Each compound is given the corresponding trivial name.
This usually originates from the compounds occurrence, its
first preparation or its special properties.
5 2
1
N
H
If there is more than one type of the heteroatoms, the ring
is numbered starting at the hetroatom of the higher priority
(O>S>N) and it continues in the direction to give the other
hetroatoms the lower numbers as possible.
3
I-Common Nomenclature
• If subsituents present, their position should be identified
by the number of the atoms bearing them and then they
should be listed in alphabetical order. Br
4
3
2
5 N
1
H 2N O
5-Amino-4-bromoisoxazole
1 , 2 - D i h y d4r o - p y r i d i n e
Trivial names
N
N
N
O O N N N N
O
N
NH
N N NH2
G u a n ine
6
Trivial names
4) Saturated heterocycles
7
II- Replacement nomenclature
Table 1
Atom Prefix
S thia
N aza
P phospha 8
II- Replacement nomenclature
N
Benzene 1,4-Diazabenzene
N
N
Cyclopentadiene 1-Oxa-3-azacyclopenta -2,4-diene
O
Cyclopropane Oxacyclopropane
O
Cyclopropene N
Oxazacyclopropene
O
O
Cyclohexane 1-Oxa-4-azacyclohexane
N
H
Na p hthalene 2-Azanaphthalene
N
9
III-Hantzsch-Widman nomenclature (IUPAC)
10
Hantzsch-Widman rules for fully saturated and fully
unsaturated heterocycles
For example:
4 N1
2
3
CH 3
11
Hantzsch-Widman rules
5 2
1
N
H
4) If more than one type of hetroatoms present in the ring the name will include more
than one prefix with locants to indicate the relative position of the heteroatoms.
4
N3
5 2
1
S
6) Combine the prefix(s) and suffix together and drop the first
vowel if two vowels came together.
13
Hantzsch-Widman rules
Table 2
N-present
Ring size N-absent
ine a in ane
epine a epin epane
• This ring contains (O ,N) and (o) has higher priority than (N) and by
starting numbering the ring at (O) Prefix is 1,2-Oxaaza, but the
first vowel must be omitted to give
1,2-Oxaza
• By combining the prefix and suffix, two vowels ended up together (1,2-
oaxazaetidine), therefore the vowel on the end of the first part should be
dropped. This gives the correct name:
1,2-oxazetidine
16
Hantzsch-Widman rules
4 3
5 N N2
O
1
N
H
18
Hantzsch-Widman rules for partially unsaturated
heterocycles
Partial unsaturation in heterocyclic compounds can be
indicated by one of the following methods:
4 3 4
3N 4 5 3
5 2 2S 1 5
O 1 6 1 2
N O O
1
H
2H, 3H-Oxole 1H-Azepine 5H-1,2,3-Oxathiazole 4H-Oxin
19
Hantzsch-Widman rules for partially unsaturated
heterocycles
b) The words dihydro, or trihydro, or tetrahydro are used if
two or three or four atoms are saturated. These words are
preceded by numbers indicate the position of saturated
atoms as low as possible and followed by the corresponding
fully unsaturated Hantzsch-Widman name.
4 4 4
5 3 5 3 5 3
4 3
6 2 6 2 6 1 2 5
1 1 2
1
N N N
H H O
Table 3
-etine -etene
-oline -olene
21
Hantzsch-Widman rules for partially unsaturated
heterocycles
• Examples
2 4 3 4 3
1 1 1 5
2 2 5 2
HN HN O 1 1
N O
2 2 H
-Azetine -Oxetene
-Azoline
3 2 -Oxolene
3
4
NH 4 N 3
5 2 5 2
1 1
S
N
4
H
-1,3-Thiazoline 2 -1,3-Diazoline
22
Hantzsch-Widman rules
• Exercise:
Explain how can you name the following heterocycles.
Br
N
O
O S N N N S
23