Synthesis of polyhydroxylated 2h-azirines and 2-halo-2h-azirines from 3-azido-2,3-dideoxyhexopyranoses by alkoxyl radical fragmentation

Alonso-Cruz, C.R. and Kennedy, A.R. and Rodriguez, M.S. and Suarez, E. (2008) Synthesis of polyhydroxylated 2h-azirines and 2-halo-2h-azirines from 3-azido-2,3-dideoxyhexopyranoses by alkoxyl radical fragmentation. Journal of Organic Chemistry, 73 (11). pp. 4116-4122. ISSN 0022-3263 (http://dx.doi.org/10.1021/jo800182y)

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Abstract

The reaction of 3-azido-2,3-dideoxypyranose and 3-azido-2,3-dideoxy-2-halohexopyranose compounds with (diacetoxyiodo)benzene and iodine generated 2-azido-1,2-dideoxy-1-iodoalditols and 2-azido-1,2-dideoxy-1-halo-1-iodoalditols, respectively. These beta-iodo azides could be transformed by chemoselective dehydroiodination into 2-azido-1,2-dideoxy-4-O-formyl-pent-1-enitols and (Z,E)-2-azido-1,2-dideoxy-1-halo-4-O-formyl-pent-1-enitols in good yields. Thermolysis and photochemical studies of these vinyl azides and 1-halovinyl azides for the synthesis of polyhydroxylated 3-alkyl-2H-azirines and the hitherto unknown 2-halo-3-alkyl-2H-azirines have also been accomplished.

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