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Novel routes to 1‐aryl‐1,4‐dihydro‐3(2 H )‐isoquinolinones and 2‐substituted or 2,3‐disubstituted benzofurans by intramolecular cyclizations
Author(s) -
Katritzky Alan R.,
Lan Xiangfu,
Zhang Zhongxing
Publication year - 1993
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.5570300216
Subject(s) - chemistry , benzotriazole , intramolecular force , aldehyde , aryl , phenols , molecule , medicinal chemistry , quenching (fluorescence) , organic chemistry , stereochemistry , catalysis , alkyl , physics , quantum mechanics , fluorescence
N ‐(α‐Benzotriazolylalkyl)arylacetamides, readily available from an arylacetamide, an aldehyde and benzotriazole, undergo intramolecular cyclization under acidic conditions to give 1‐aryl‐1,4‐dihydro‐3(2 H )‐isoquinolinones in good to excellent yields. Similarly, 2‐(benzotriazol‐1‐yl)‐2‐( o ‐hydroxyphenyl)ethanols, obtained by lithiation of 2‐(benzotriazol‐1‐ylmethyl)phenols followed by quenching with aldehydes or ketones, eliminate a molecule of water and a molecule of benzotriazole yielding 2‐substituted and 2,3‐disubstituted benzofurans.