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1,3-azaphospholo[5,1-a]isoquinolines

✍ Scribed by Raj K. Bansal; Leena Hemrajani; Neelima Gupta

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
218 KB
Volume
10
Category
Article
ISSN
1042-7163

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✦ Synopsis

In a one pot synthesis, 1,3-azaphospholo [5,1-a]isoquinoline (4) was obtained from the reaction of N-(alkoxycarbonylmethyl)isoquinolinium bromide (1) with PCl 3 in the presence of (C 2 H 5 ) 3 N. A crossed reaction confirms the formation of 4 proceeding via a 1,5-electrocyclization. Compound 4 undergoes ‫]4ם2[‬ cycloaddition with 2,3-dimethyl-1,3-butadiene in the presence of sulfur. The influence of the substituent group on the reactivity of the C‫ב‬P-moiety in the 1,3-azaphospholo ring toward ‫]4ם2[‬ cycloaddition is corroborated by semiempirical PM3 calculations.

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Microwave-assisted synthesis and diels–a
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