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Synthesis and 1,3-dipolar cycloaddition reactions of N-Aryl-C, C-dimethoxycarbonylnitrones

✍ Scribed by Yukihiko Tomioka; Chie Nagahiro; Yumiko Nomura; Hiroshi Maruoka

Publisher
Journal of Heterocyclic Chemistry
Year
2003
Tongue
English
Weight
69 KB
Volume
40
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Arylnitroso compounds 1–3 easily reacted with dimethyl bromomalonate to give the corresponding N‐aryl‐C,C‐dimethoxycarbonylnitrones (4–6). Treatment of C,C‐dimethoxycarbonyl‐N‐( 1‐naphthyl)nitrone (4) with acetylene compounds (dimethyl acetylenedicarboxylate, methyl 2‐butynoate or ethyl phenylpropiolate) caused 1,3‐dipolar cycloaddition to furnish the corresponding 1__H__‐benz[g]indolines (7a‐c). In a similar manner, the reactions of nitrones 5 and 6 with acetylene compounds afforded the corresponding indolines 9a‐c and 11a‐c together with 4‐oxazolines 13a‐c and 14a‐c.

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Investigation of cycloadditions of C-aryl-N-(4-chlorophenyl)nitrones to N-cinnamoyl piperidines was carried out. Two diastereoisomeric and one regioisomeric cycloadducts, and in some cases ring-opened compounds were characterized by spectroscopic and X-ray data. Molecular modelling was carried out f