Synthesis of polyhydroxylated 2H-azirines and 2-halo-2H-azirines from 3-azido-2,3-dideoxyhexopyranoses by alkoxyl radical fragmentation.
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-2 H-azirines and the hitherto unknown 2-halo-3-alkyl-2 H-azirines have also been accomplished.
Alonso-Cruz
Carmen R
CR
Instituto de Productos Naturales y Agrobiología, Consejo Superior de Investigaciones Cientificas, Carretera de La Esperanza 3, La Laguna, Tenerife, Spain.
Kennedy
Alan R
AR
Rodríguez
María S
MS
Suárez
Ernesto
E
D001389:Azirines / Q000138:chemical synthesis*; D005609:Free Radicals / Q000737:chemistry; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D011714:Pyrans / Q000737:chemistry*
D001389:Azirines; D005609:Free Radicals; D011714:Pyrans