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New synthesis of condensed heterocycles from isoxazole derivatives VI . 2,5‐Dimethyl‐3‐aeetyl‐7‐amino‐1 H ‐pyrrolo[3,2‐b] pyridine
Author(s) -
Aiello E.,
Dattolo G.,
Cirrincione G.,
Plescia S.,
Daidone G.
Publication year - 1978
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570150402
Subject(s) - chemistry , isoxazole , nitration , pyridine , ring (chemistry) , hydrogenolysis , pyrrole , acetic anhydride , medicinal chemistry , nitro , oxazole , acetic acid , stereochemistry , organic chemistry , catalysis , alkyl
A new synthesis of pyrrolo[3,2‐ b ] pyridine starting with pyrrole ring is described. The procedure allows the synthesis of 4‐azaindoles bearing a sensitive group at C‐7. The nitration of 4b with nitric acid and acetic anhydride at −15° gave 5 . The hydrogenation of 5 led to simultaneous reduction of N ‐hydroxy and nitro groups and to hydrogenolysis of the isoxazole nucleus, affording an appropriate chain of atoms to building up the pyrrolo[3,2‐ b ] pyridine ring.