Heterocyclic ring

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Heterocyclic Ring

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Heterocyclic ring

  1. 1. 04/30/14 1
  2. 2. 04/30/14 2
  3. 3. Heterocyclic Ring 04/30/14 3
  4. 4.  A heterocyclic compound is a cyclic compound that has atoms of at least two different elements as members of its ring(s). The counterparts of heterocyclic compounds are homocyclic compounds, the rings of which are made of a single element.  Although heterocyclic compounds may be inorganic, most contain at least one carbon atom, and one or more atoms of elements other than carbon within the ring structure, such as sulfur, oxygen, or nitrogen. 04/30/14 4
  5. 5.  Classification based on electronic structure  5-Membered rings  6-Membered rings 04/30/14 5
  6. 6.  5-Membered rings i.e – Furan, Thiphene, Pyrrole  6-Membered rings i.e – Pyridine, Pyran  Benzofused rign  i.e – Indole ring, Quinoline ring etc 04/30/14 6
  7. 7.  With heterocycles containing five atoms, the unsaturated compounds are frequently more stable because of aromaticity. i.e - Puran,, Pyrrole,Thiphene etc  Puran, It is an aromatic compound. Because it has Resonance structure. 04/30/14 7
  8. 8. Pyrrole ring It is also a aromatic compound. It show aromaticity in its structure. Synthesis of Pyrrole: Pyrrole can be synthesized from  mucic acid  Acetylene  Paal-knorr synthesis  Succinamide  Furan etc 04/30/14 8
  9. 9.  Pyrole ring is acidic.  Pyrrol donate proton in reaction for this reason,it is acidic in nature.  Chemical Reaction of Pyrrole .  It gives Electrophilic substitution reaction 04/30/14 9
  10. 10.  Six-membered rings with a single heteroatom i.e – Pyridine  Synthesis of pyridine: 04/30/14 10
  11. 11.  Chemical reaction of Pyridine  -Electrophilic Substitution reaction of pyridine. 04/30/14 11
  12. 12.  Benzofuse ring such as Indole ring, Quinoline ring, Isoquinoline ring.  Indole synthesis  Leigngruber-Batcho indole synthesis  Fisher indole synthesis 04/30/14 12
  13. 13.  Electrophilic Substitution reaction 04/30/14 13
  14. 14.  Oxidation of indole  Due to the electron-rich nature of indole, it is easily oxidized. Simple oxidants such as N- bromosuccinimide will selectively oxidize indole 1 to oxindole (4 and 5). 04/30/14 14
  15. 15. 04/30/14 15
  16. 16.  Halogenation reaction of Isoquinoline 04/30/14 16
  17. 17. 04/30/14 17

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