Convenient synthesis of 1,2-dihydroquinoline-3-carboxylicacid and 2H-1-benzothiopyran-3-carboxylic acid derivatives

Authors
Kobayashi, K Nakahashi, R Shimizu, A Kitamura, T Morikawa, O Konishi, H
Citation
K. Kobayashi et al., Convenient synthesis of 1,2-dihydroquinoline-3-carboxylicacid and 2H-1-benzothiopyran-3-carboxylic acid derivatives, J CHEM S P1, (11), 1999, pp. 1547-1551
Citations number
50
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
11
Year of publication
1999
Pages
1547 - 1551
Database
ISI
SICI code
0300-922X(19990607):11<1547:CSO1A2>2.0.ZU;2-9
Abstract
A new and efficient method for the preparation of 1,2-dihydroquinoline-3-ca rboxylic acid derivatives via a magnesium amide-induced sequential conjugat e addition-aldol type condensation reaction between 2-(alkylamino)phenyl ke tones and alpha,beta-unsaturated carboxylic acid derivatives, followed by s imple dehydration, is described. The method can be applied to the synthesis of 2H-1-benzothiopyran-3-carboxylic acid derivatives using 2-mercaptobenzo phenone in place of 2-(alkylamino)phenyl ketones.