Highly regioselective nucleophilic/cycloaddition reactions of W-arylamino l,3-diazabuta-l,3-dienes with a-nitrosostyrenes: Synthesis of functionalised imidazoles, and imidazole oxides

Arun Sharma, Geeta Hundal, Sangeeta Obrai, Mohinder P. Mahajan

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Abstract

The a-nitrosostyrenes 2, generated in situ from a-halogeno oximes, underwent regioselective cycloadditon/ nucleophilic reactions with W-arylamino l,3-diazabuta-l,3-dienes 1 leading to a mixture of imidazoles, and cyclic nitrones shown to have structures 3, and 4, respectively, by X-ray crystallographic analysis. The structure 4 for cyclic nitrones was also supported by their 1,3-dipolar cycloaddition with dimethyl acetylenedicarboxylate (DM AD). The thermolysis of nitrones 4 gives imidazoles 3 via oxadiazine intermediates 6.

Original languageEnglish (US)
Pages (from-to)615-619
Number of pages5
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number5
DOIs
StatePublished - 1999

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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