Fused heterocyclic compound indole

This slide discusses about basic indole nucleus, its chemistry, synthesis, reactions and medicinal uses of Indolyl derivatives..Indole is basically fused heterocyclic compound

1. Fused Heterocyclic compound- Indole Lecture by S.Mathivanan ., M.Pharm Assistant professor Pharmacy

2. Indole  is an  aromatic   heterocyclic   organic compound  with formula   C 8 H 7 N . It has a bicyclic structure, consisting of a six- membered   benzene  ring fused to a five- membered   pyrrole   ring. The name  indole  is a  portmanteau  of the words  ind igo   and   ole um , since indole was first isolated by treatment of the indigo dye with oleum . Other names 2,3-Benzopyrrole , ketole , 1-benzazole IUPAC : 1H-Indole

3. The  amino acid   tryptophan  is an indole derivative and the precursor of the  neurotransmitter   serotonin . Tryptophan Seratonin

4. Indole chemistry began to develop with the study of the dye  indigo . Indigo can be converted to   isatin  and then to  oxindole . Then, in 1866,  Adolf von Baeyer  reduced  oxindole  to indole using   zinc  dust .  In 1869, he proposed a formula for indole . Certain indole derivatives were important dyestuffs until the end of the 19th century. In the 1930s, interest in indole intensified when it became known that the indole substituent is present in many important  alkaloids   ( e.g.,  tryptophan  and  auxins ), and it remains an active area of research today Indigo dye Baeyer’s Indole formula

5. Physical properties Indole is a  solid  at room temperature. It occurs naturally in human  feces  and has an intense fecal  odor . At very low concentrations, however, it has a flowery smell ,  and is a constituent of many  perfumes . It also occurs in  coal tar . The corresponding  substituent   is called   indolyl . Density : 1.1747 g/cm 3 Melting point : 52 to 54 °C Boiling point 253 to 254 °C

6. 1. Aro m at i c Chemical Properties Unlike most  amines , indole is not  basic : just like  pyrrole , the aromatic character of the ring means that the  lone pair  of electrons on the nitrogen atom is not available for protonation . Strong acids such as  hydrochloric acid  can, however,  protonate   indole . Indole is primarily protonated at the C3, rather than N1, owing to the  enamine -like reactivity of the portion of the molecule located outside of the  benzene  ring. The protonated form has a  p K a  of −3.6.

7. Synthesis 1. Fischer indole synthesis

8. Synthesis 1. Fischer indole synthesis Mechanism

9. Synthesis 1. Fischer indole synthesis Mechanism

10. Synthesis 1. Fischer indole synthesis

11. Synthesis 2. Bischler–Möhlau indole synthesis

12. Synthesis 3. Madelung synthesis

13. Synthesis 3. Madelung synthesis E.g .

14. Reactions 1. Electrophilic addition to N

15. Reactions 2. Electrophilic aromatic substitution

16. Reactions 2. Electrophilic aromatic substitution

17. Reactions 2. Electrophilic aromatic substitution

18. Reactions 2. Electrophilic aromatic substitution

19. Reactions 2. Electrophilic aromatic substitution

20. Reactions 3. Reduction reactions

21. Reactions 4. Nucleophilic substitution

22. Medicinal uses (1) Indole alkaloids :

23. Medicinal uses

24. Medicinal uses

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