Nomenclature of Heterocyclic Compounds follows IUPAC rules, naming based on ring size, heteroatom type, and saturation or unsaturation.
Heterocycles are named using common (trivial) names or systematic IUPAC names.
-
Common/Trivial Names
- These are historical or widely accepted names, commonly used for simple or well-known heterocycles.
- Examples:
- Aziridine (3-membered ring with N)
- Oxirane (epoxide, 3-membered ring with O)
- Pyrrole (5-membered, aromatic, with N)
- Furan (5-membered, aromatic, with O)
- Thiophene (5-membered, aromatic, with S)
- Pyridine (6-membered, aromatic, with N)
-
IUPAC Nomenclature
- The IUPAC system uses standardized prefixes and suffixes:
Prefixes for Heteroatoms:
Heteroatom | Prefix |
Oxygen | oxa- |
Nitrogen | aza- |
Sulfur | thia- |
Phosphorus | phospha- |
Selenium | selena- |
Silicon | sila- |
Suffixes Based on Ring Size and Saturation:
Ring Size | Saturated Suffix | Unsaturated Suffix |
3 | -irine | -irene |
4 | -etidine | -ete |
5 | -olidine | -ole |
6 | -ane | -ine |
Naming Rules:
-
- Identify the ring size and saturation.
- Assign prefixes based on the type and position of heteroatoms.
- Choose the appropriate suffix.
- Number the ring to give the heteroatoms the lowest possible locants.
- In complex cases, consider the principal ring and use fusion nomenclature for attached rings.
Examples:
-
- Imidazole
- 5-membered aromatic ring
- Contains two nitrogen atoms
- Common and IUPAC-accepted name
- Morpholine
- 6-membered saturated ring
- Contains one oxygen and one nitrogen
- IUPAC name: 1-oxa-4-azacyclohexane
- Common name: Morpholine
- Indole
- Fused bicyclic compound: benzene + pyrrole
- IUPAC name: 1H-indole
- Imidazole
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