77541-41-4Relevant articles and documents
1,3-DIPOLAR CYCLOADDITION OF C-BENZOYL-N-PHENYLNITRONE WITH FURAN DERIVATIVES. ANOMALOUS DEHYDROGENATION OF CYCLOADDUCTS WITH 2,3-DICHLORO-5,6-DICYANO-1,4-BENZOQUINONE
Fisera, Lubor,Lesko, Jan,Dandarova, Miloslava,Kovac, Jaroslav
, p. 3546 - 3556 (2007/10/02)
C-Benzoyl-N-phenylnitrone reacted with 2-R-substituted (R=phenyl,CH2OH,CH2OCOCH3,CH2SH)furan derivatives at 55 deg C by a 3-dipolar cycloaddition reaction to the unsubstituted furan double bond to give mono- and bisadducts. 2,5-Dimethylfuran afforded monoadduct only.Dehydrogenations of monoadducts of 5-R-2-phenyl-3-benzoyl-3a,6a-dihydrofuroisoxazolines with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone proceeded anomously at 60 deg C: dehydrogenation followed by electrocyclic opening afforded the corresponding ketonitrones.This method of dehydrogenation offersa new preparation of nitrones and further exemplifies the exploitation of products of 1,3-dipolar cycloaddition for synthetic purposes.