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Synthesis of 2-substituted-3-nitroimidazo[1,2-b]pyridazines as potential biologically active agents

✍ Scribed by Thierry Terme; Joséa Maldonado; Michel P. Crozet; Patrice Vanelle; Christophe Galtier; Alain Gueiffier

Publisher: Journal of Heterocyclic Chemistry
Year: 2002
Tongue: English
Weight: 56 KB
Volume: 39
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570390125

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✦ Synopsis

Abstract

A new heterocyclic reductive alkylating agent, 6‐chloro‐2‐chloromethyl‐3‐nitroimidazo[1,2‐b]pyridazine, was synthesized for the first time. It was shown to react under phase‐transfer catalysis conditions with 2‐nitropropane anion by an S~RN~1 mechanism to give excellent yield of isopropylidene derivative formed from a base‐promoted nitrous acid elimination of C‐alkylation product. Extension of this S~RN~1 reaction to various nitronate anions led to a new class of 3‐nitroimidazo[1,2‐b]pyridazine derivatives bearing a trisub‐stituted double bond at the 2‐position.

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