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Synthesis of 4 H ‐furo[3,2 ‐b ]indole derivatives A new heterocyclic ring system
Author(s) -
Tanaka Akira,
Yakushijin Kenichi,
Yoshina Shigetaka
Publication year - 1977
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.5570140605
Subject(s) - chemistry , indole test , formylation , furan , ring (chemistry) , wittig reaction , deoxygenation , stereochemistry , medicinal chemistry , organic chemistry , catalysis
4 H ‐Furo[3,2‐ b ]indole (III) was prepared from deoxygenation of 2‐(2‐nitrophenyl)furan (II) with triethyl phosphite and thermolysis of 2‐(2‐azidophenyl)furan (VI). 4 H ‐ or 4‐alkylfuro [3,2 ‐b ]indole‐2‐carboxaldehydes (VIII, IXa ‐c ) were obtained by Vilsmeier formylation of the corresponding furo[3,2‐ b ]indoles (III, VIIa ‐c ). 4 H ‐Furo[3,2‐ b ]indole‐2‐carboxaldehyde (VIII) was submitted to the Cannizzaro, Wittig and reduction reactions. The Shiff's bases were obtained by the reaction of 4‐ethylfuro[3,2‐ b ]indole‐2‐carboxaldehyde (IXb) with amines. J. Heterocyclic Chem. , 14, 975 (1977)