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Studies on furan derivatives. X . Preparation of 2‐Methylfuro[2,3‐ c ]quinoline Derivatives
Author(s) -
Usui Toshinao,
Tsubone Yasuo,
Tanaka Akira
Publication year - 1985
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.5570220348
Subject(s) - quinoline , chemistry , isomerization , azide , furan , medicinal chemistry , nucleophile , sodium azide , organic chemistry , catalysis
4‐Chloro‐2‐methylfuro[2,3‐ c ]quinoline (IV) was synthesized from ethyl 3‐(2‐nitrophenyl)‐5‐methyl‐2‐furoate and IV was allowed to react with some nucleophiles to afford the corresponding 4‐substituted 2‐methylfuro‐[2,3‐ c ]quinoline derivatives, respectively. On treatment of IV with potassium azide in dimethylsulfoxide, 2‐methylfuro[2,3‐ c ]tetrazolo[1,5‐ a ]quinoline was formed path azido‐tetrazolo isomerization. 2‐Methylfuro‐[2,3‐ c ]quinoline was prepared by the reduction of IV.