HETROCYCLES HAS MANY APPLICATIONS DISCUSS?

Heterocyclic Compound

A heterocyclic compound has at least two different elements as a member of its ring.

The most common hetero atoms found on a cyclic ring are Oxygen (O), Nitrogen (N) and Sulphur (S).

Classification of Heterocyclic Compound

Based on the electronic arrangement, we can classify Heterocyclic compounds into two types:

1.Aliphatic Heterocyclic Compound

2.Aromatic Heterocyclic Compound

Aliphatic Heterocyclic Compound

-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 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 Compound

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

Based on the number of heteroatoms present, we can further classify it 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 Compound

These heterocyclic compounds contain four atoms which may be saturated or unsaturated.
Based on the number of heteroatoms present, we can further classify it 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 Compound

 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 it 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 Compound

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 it 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

1. Heterocyclic compounds are used in agrochemicals and pharmaceuticals industries.

2. Heterocyclic compounds are used as starting materials in the synthesis of organic compounds.

3.Heterocyclic compounds are used in corrosion inhibitors, sanitisers, anti-ordinates, and developers.

4. Heterocyclic compounds are used in pesticides, dyes, plastics.

QUESTION 2

DESCRIBE THE HANZTCH SYNTHESIS OF PYRIDINE AND THE MECHANISM OF THE REACTION

The Hantzsch pyridine synthesis or Hantzsch dihydropyridine synthesis is a multi-component organic

reaction between an aldehyde such as formaldehyde, 2 equivalents of a β-keto ester such as ethyl
acetoacetate and a nitrogen donor such as ammonium acetate or ammonia.

Hantzsch Dihydropyridine (Pyridine) Synthesis

This reaction allows the preparation of dihydropyridine derivatives by condensation of an aldehyde with
two equivalents of a β-ketoester in the presence of ammonia. Subsequent oxidation (or
dehydrogenation) gives pyridine-3,5-dicarboxylates, which may also be decarboxylated to yield the
corresponding pyridines.
Mechanism of the Hantzsch Dihydropyridine Synthesis

The reaction can be visualized as proceeding through a Knoevenagel Condensation product as a key
intermediate:

A second key intermediate is an ester enamine, which is produced by condensation of the second
equivalent of the β-ketoester with ammonia: