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Synfacts 2010(10): 1115-1115
DOI: 10.1055/s-0030-1258613
DOI: 10.1055/s-0030-1258613
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
NHC-Mediated [2+2] Cycloaddition Route to Nitro-β-thiolactams
C. Awasthi, L. D. S. Yadav*
University of Allahabad, India
Further Information
Publication History
Publication Date:
22 September 2010 (online)
Significance
Reported is the synthesis of nitro-β-thiolactams by the N-heterocyclic carbene (NHC)-mediated [2+2] cycloaddition of trans-nitroolefins with isocyanates. The reaction did not proceed in the absence of the NHC. Through analogy with the well-known reaction of ketenes with imines, it was suggested that the most likely mechanism involves NHC attack on the isocyanate, followed by subsequent Michael-type addition onto the nitro alkene, then ring closure to give the final compound with regeneration of the catalyst.