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Reaction of ω-carbonyl substituted 1,3,3-trimethyl-2-methyleneindolines with phosphorus(III) halides

✍ Scribed by Alexej A. Chekotylo; Alexandr N. Kostyuk; Alexandr M. Pinchuk; Andrej A. Tolmachev

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
104 KB
Volume
14
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

The phosphorylation of N‐benzoyl‐2‐(1,3,3‐trimethyl‐2‐methyleneindoline)acetamide (2) and ω‐(3‐dimethylamino)benzoyl‐1,3,3‐trimethyl‐2‐methyleneindoline (6) with phosphorus(III) halides resulted in the formation of 2,3‐dihydro‐4__H__‐1,5,2‐oxazaphosphinin‐4‐one and 1,2‐dihydro‐3__H__‐phosphindol‐3‐one systems, respectively. The properties of the obtained compounds were studied. Further cyclization of 1,2‐dihydro‐3__H__‐phosphindol‐3‐one into dihydrophosphindolo[3,2‐c]pyrazole was carried out. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:23–28, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10060

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## Abstract 2‐(3‐Methyl‐1,3‐diazabuten‐1‐yl)‐3‐ethoxycarbonylthiophenes are phosphorylated with phosphorus(III) halides in basic media at position 5 of the thiophene ring. Up to three heteroaromatic substituents can be introduced one by one at the same phosphorus atom. On this basis, mono‐, bis‐, a