Synthesis of functionalised cyclic nitrones via regioselective and unusual [3 + 2] cycloadditions of α-nitrosostyrenes with 1,3-diazabuta-1,3-dienes and imines

Arun Sharma, Sujit N. Mazumdar, Mohinder P. Mahajan

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Abstract

The α-nitrosostyrenes 2, generated in situ from α-halogeno oximes, undergo regioselective [3 + 2] cycloaddition with 1,3-diazabuta-1,3-dienes 1 and 5 leading to the cyclic nitrones 3 and 6, respectively. Similarly, the cyclic nitrones 12 are also formed in reactions of 2 with the trisubstituted amidines 11. Thermolysis of the nitrones 3 and 12d-f gives imidazole derivatives 13. The nitrones 6, on the other hand, on thermolysis under similar conditions, give the amidine derivatives 17. Interestingly, the treatment of both 3 and 6 with NaBH4 in methanol and the reactions of 2 with N-arylbenzamidines also yield the imidazole derivatives 13.

Original languageEnglish (US)
Pages (from-to)3065-3070
Number of pages6
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number20
DOIs
Publication statusPublished - Oct 21 1997

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All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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