SUBJECT : PHARMACEUTICAL ORGANIC CHEMISTRY

III [BP401T]
ACADEMIC YEAR : 2023 – 2024
COURSE : II/IV B.PHARMACY 4th SEM
GROUP NO : 7

SUBMITTED BY :

S.NO NAME REGISTERED TOPIC

NUMBER

1. S. PRASANNA Y22BPH140095 NOMENCLATURE

AND
CLASSIFICATION
OF
HETEROCYCLIC
COMPOUNDS

SUBMITTED TO:

Mrs.K.SARITHA MAM
ASSISTANT PROFESSOR
Mrs.Sk.JARINA MAM
ASSISTANT PROFESSOR
DEPARTMENT OF PHARMACEUTICAL CHEMISTRY

SIGNATURE OF STUDENT SIGNATURE OF STAFF INCHARGE

NOMENCLATURE AND CLASSIFICATION OF HETEROCYCLIC
COMPOUNDS

NOMENCLATURE

Nomenclature rules for heterocyclic compounds are based on the systematic naming of the
ring structure, considering both the heteroatoms (atoms other than carbon) and the
connectivity within the ring. Here are some key guidelines:

1. Identify the Parent Heterocycle: Determine the parent structure based on the ring size
and the type and number of heteroatoms (such as nitrogen, oxygen, sulfur, etc.).

2.Ring Size and Suffix:The ring size is indicated by using the Greek prefixes (e.g.,
pyrrolidine, pyridine) or numerical prefixes (e.g., azepine for a 7-membered ring).

3. Heteroatoms: Heteroatoms are named with prefixes before the parent ring name (e.g.,
pyrrole for a 5-membered ring containing one nitrogen atom).

4. Numbering:Number the ring atoms to give the lowest set of locants to the heteroatoms,
followed by substituents. The numbering usually starts at the heteroatom and proceeds to give
the next substituents the lowest possible locants.

5. Substituents: Substituents on the ring are named as usual and are located by number. The
prefix "N-" is used for substituents attached to nitrogen in the ring.

6. Multiple Substituents: Use prefixes (di-, tri-, tetra-) to indicate multiple identical
substituents. If different substituents are present, list them alphabetically before the name of
the parent heterocycle.

7. Bridged Heterocycles: In bridged heterocycles, indicate the bridge using appropriate

nomenclature, specifying the number of atoms in the bridge.

8. Fused Heterocycles:Fused heterocyclic systems are named by combining the names of the
fused rings, indicating fusion through common atoms.

9. Spiro Heterocycles: These are named by listing the heterocyclic rings in order of ring size
and specifying the connection point.

10. Heteroaromatic Compounds: If the heterocyclic compound exhibits aromaticity (like

pyrrole or pyridine), aromaticity should be considered in the nomenclature.
CLASSIFICATION OF HETEROCYCLIC COMPOUNDS
Based on the electronic arrangement, we can classify Heterocyclic compounds into two
types:

 Aliphatic Heterocyclic Compounds

 Aromatic Heterocyclic Compounds

Aliphatic Heterocyclic Compounds

 Aliphatic heterocyclic compounds are those cyclic heterocycles that do not contain
any double bond.
 The properties of aliphatic heterocyclic compounds are mainly affected due to ring
strain.
 Examples of aliphatic heterocyclic compounds are Aziridine, Ethylene Oxide,
Thiirane, Oxetane, Azetidine, Thietane, Tetrahydrofuran (THF), Dioxane, Pyrrolidine,
Piperidine, etc.

Aromatic Heterocyclic Compound

 Aromatic heterocyclic compounds, as the name suggests, are cyclic aromatic

compounds.
 Aromatic Heterocyclic compounds obey Huckels Rule, i.e.
 It should be cyclic.
 It should be planar.
 It should not contain any sp3 hybridised atoms.
 It must have (4n+2) 𝛑 electrons.
 Aromatic Heterocyclic compounds are analogous to Benzene.
 Examples: Furan, Pyrrole, Thiophene, Indole, Benzofuran, Carbazole, Quinoline,
Isoquinoline, Imidazole, Oxazole, Pyrazole, Pyridazine, Pyrimidine, Purine, etc.
Based on structure, we can classify Heterocyclic compounds into five types:

1. Three-Membered Heterocyclic Compounds

2. Four-Membered Heterocyclic Compounds
3. Five-Membered Heterocyclic Compounds
4. Six-Membered Heterocyclic Compounds
5. Condensed or Fused Heterocyclic Compounds

Three-Membered Heterocyclic Compounds

These heterocyclic compounds contain three atoms which may be saturated or unsaturated.

Based on the number of heteroatoms present, we can further classify them into two
categories:

Heterocyclic compounds with one heteroatom.

 As the name suggests, it has one heteroatom present in its ring.

 Examples: Aziridine, Oxirane, Thiirane, Azirine, Oxirene and Thiirene.
Heterocyclic compounds with more than one heteroatom.

 As the name suggests, it has more than one heteroatom present in its ring.
 The heteroatom atom in the ring can be the same or different.
 Examples: Diaziridine and Oxiaziridine.

Four-Membered Heterocyclic Compounds

These heterocyclic compounds contain four atoms which may be saturated or unsaturated.

Based on the number of heteroatoms present, we can further classify them into two
categories:

Heterocyclic compounds with one heteroatom.

 As the name suggests, it has one heteroatom present in its ring.

 Examples: Azetidine, Oxetane, Thietane, Azete, Oxete, Thiete, etc

Heterocyclic compounds with more than one heteroatom.

 As the name suggests, it has more than one heteroatom present in its ring.
 The heteroatom atom in the ring can be the same or different.
 Examples: Diazetidine and Dioxetane.
Five-Membered Heterocyclic Compounds

These heterocyclic compounds are derived from Benzene by replacing a C=C bond with a
hetero atom having a lone pair of electrons.

Based on the number of heteroatoms present, we can further classify them into two
categories:

Heterocyclic compounds with one heteroatom.

 As the name suggests, it has one heteroatom present in its ring.

 Examples: furan, pyrrole and thiophene.

Heterocyclic compounds with more than one heteroatom.

 As the name suggests, it has more than one heteroatom present in its ring.
 The heteroatom atom in the ring can be the same or different.
 Examples: Pyrazole, Imidazole, Oxazole, Thiazole, Triazole and Tetrazole, etc.
Six-Membered Heterocyclic Compounds

These heterocyclic compounds are derived from Benzene by replacing one of the Carbon
with a hetero atom having a lone pair of electrons.

Based on the number of heteroatoms present, we can further classify them into two
categories:

Heterocyclic compounds with one heteroatom.

 As the name suggests, it has one heteroatom present in its ring.

 Examples: Pyridine, Pyran, Thiopyran, etc.

Heterocyclic compounds with more than one heteroatom.

 As the name suggests, it has more than one heteroatom present in its ring.
 The heteroatom atom in the ring can be the same or different.
 Examples: Pyridazine, Pyrimidine, Pyrazine, etc.
Condensed or Fused Heterocyclic Compound

 Condensed or Fused Heterocyclic Compound contains two or more fused rings.

 Condensed or Fused Heterocyclic Compounds can be partly carbocyclic or partly
heterocyclic.
 Examples: Indole, Quinoine, Isoquionoline, Cabazole, etc.
 Condensed or Fused Heterocyclic Compounds can also be completely heterocyclic.
 Examples: Purine, Pteridine, etc.

Applications of Heterocyclic Compound

 Heterocyclic compounds are used in agrochemicals and pharmaceuticals industries.

 Heterocyclic compounds are used as starting materials in the synthesis of organic
compounds.
 Heterocyclic compounds are used in corrosion inhibitors, sanitisers, anti-ordinates,
and developers.
 Heterocyclic compounds are used in pesticides, dyes and plastics