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Synthesis of Furo[2,3‐ c ]isoquinoline Derivatives
Author(s) -
Ito Kazuo,
Yakushijin Kenichi,
Yoshina Shigetaka,
Tanaka Akira,
Yamamoto Katsumi
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.5570150224
Subject(s) - chemistry , isoquinoline , curtius rearrangement , azide , double bond , alkylation , medicinal chemistry , thermal stability , stereochemistry , organic chemistry , catalysis
2‐Methylfuro [2,3‐ c ] isoquinolin‐5(4 H )one (X) and 1‐phenylfuro[2,3‐ c ] isoquinolin‐5(4 H )one (XI) were prepared from thermal cyelization via the Curtius rearrangement of 5‐methyl‐3‐phenyl‐2‐furoyl azide (VI) and 3,4‐diphenyl‐2‐furoyl azide (VII), respectively. Stability against acid, alkylation and conversion of the NHCO group to a C=N double bond of X and XI, which were synthesized, are described. Also, 5‐substituted furo[2,3‐ c ] isoquinolines (XVIIIa‐c) and (XIXa‐c) were prepared.