NOVEL ROUTES TO 1-ARYL-1,4-DIHYDRO-3(2H)-ISOQUINOLINONES AND 2-SUBSTITUTED OR 2,3-DISUBSTITUTED BENZOFURANS BY INTRAMOLECULAR CYCLIZATIONS

Citation
Ar. Katritzky et al., NOVEL ROUTES TO 1-ARYL-1,4-DIHYDRO-3(2H)-ISOQUINOLINONES AND 2-SUBSTITUTED OR 2,3-DISUBSTITUTED BENZOFURANS BY INTRAMOLECULAR CYCLIZATIONS, Journal of heterocyclic chemistry, 30(2), 1993, pp. 381-387
Citations number
38
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
0022152X
Volume
30
Issue
2
Year of publication
1993
Pages
381 - 387
Database
ISI
SICI code
0022-152X(1993)30:2<381:NRT1A2>2.0.ZU;2-W
Abstract
N-(alpha-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(2H)-i soquinolinones in good to excellent yields. Similarly, 2-(benzotriazol -1-yl)-2-(o-hydroxyphenyl)ethanols, obtained by lithiation of 2-(benzo triazol-1-ylmethyl)phenols followed by quenching with aldehydes or ket ones, eliminate a molecule of water and a molecule of benzotriazole yi elding 2-substituted and 2,3-disubstituted benzofurans.