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Synfacts 2007(10): 1026-1026
DOI: 10.1055/s-2007-968981
DOI: 10.1055/s-2007-968981
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Tetrazole and Oxadiazole Sulfoximines
O. G. Mancheño, C. Bolm*
RWTH Aachen, Germany
Further Information
Publication History
Publication Date:
07 November 2007 (online)


Significance
Reported are reasonably efficient syntheses of tetrazole and oxadiazole sulfoximines. The N-cyano sulfoximines 1, which can be prepared from readily available sulfides and cyanamide in two steps or by direct cyanation of the NH-sulfoximines, undergo a [2+3] cycloaddition reaction with NaN3 to afford tetrazole sulfoximines 2, which upon treatment with TFAA rearrange into 5-substituted oxadiazole sulfoximines 3. The reaction sequence starting from a chiral NH-sulfoximine proceeds without loss of enantiopurity.