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A General Approach to the Synthesis of Substituted Isoxazolo[4,3‐ c ]quinolines via Chalcones
Author(s) -
Madapa Sudharshan,
Sridhar Divya,
Yadav Gaya P.,
Maulik Prakas R.,
Batra Sanjay
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700268
Subject(s) - chemistry , intramolecular force , nitro , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , alkyl
A general and practical approach to the synthesis of substituted isoxazolo[4,3‐ c ]quinolines from the substituted isoxazolines obtained by 1,3‐dipolar cycloadditions between2‐nitrobenzonitrile oxide and chalcones is described. SnCl 2 · 2H 2 O‐mediated reduction of the nitro group, followed by intramolecular cyclization involving the amino and the keto groups in these substrates, furnished mixtures ofisoxazolo[4,3‐ c ]quinolines and 3,5‐dihydroisoxazolo[4,3‐ c ]quinolines. In contrast, the reduction of these substrates with Fe/AcOH unexpectedly yielded 3‐benzoylquinolin‐4‐ylamine derivatives.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)