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Phosphorylation of 2-(3-methyl-1,3-diazabuten-1-yl)-3-ethoxycarbonylthiophenes with phosphorus(III) halides

✍ Scribed by Alexandr M. Pinchuk; Svetlana A. Kovalyova; Sergey P. Ivonin; Anatoliy S. Merkulov; Tamara N. Kudrya; Alexandra A. Chaikovskaya; Andrey A. Tolmachev

Publisher
John Wiley and Sons
Year
2001
Tongue
English
Weight
265 KB
Volume
12
Category
Article
ISSN
1042-7163

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✦ Synopsis

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‐, and trishetaryl substituted P(III) and P(V) derivatives have been obtained. Phosphorylated 2‐(N,N‐dimethylformamidino)‐3‐ethoxycarbonylthiophenes provide a synthetic access to phosphorylated thienopyrimidines. © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:641–651, 2001

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## 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‐dihyd