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

Abstract

AbstractA 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 SRN1 mechanism to give excellent yield of isopropylidene derivative formed from a base‐promoted nitrous acid elimination of C‐alkylation product. Extension of this SRN1 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.