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C-phosphorylation of 5,10-dimethyl-5,10-dihydrophenazine and its carbo- and heteroanalogs

✍ Scribed by Sergei P. Ivonin; Svetlana D. Kopteva; Viktor N. Serdyuk; Andrei A. Tolmachev; Aleksandr M. Pinchuk

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

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✦ Synopsis

Abstract

This study covers phosphorylation of heterocyclic analogues of N‐methyldiphenylamine with phosphorus tribromide in pyridine solution. The reaction is found to proceed regioselectively in accordance with the orienting effect of the amino group. Mono and bis‐phosphorylated derivatives of the heterocycles have been isolated and characterized. It is pointed out that the heterocyclic systems under study exhibit reduced reactivity in electrophilic phosphorylation as compared to N‐methyldiphenylamine. The results of calculations by the PM3 method are reported for the starting molecules and their σ‐complexes. © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:652–657, 2001

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