173065-27-5Relevant articles and documents
Unusual reactivity of (vinylimino)phosphoranes and their utility in the preparation of pyridine and dihydropyridine derivatives
Molina, Pedro,Pastor, Aurelia,Vilaplana, Maria Jesus
, p. 8094 - 8098 (1996)
New reactions of (vinylimino)phosphoranes with aldehydes involving an initial nucleophilic attack of the β-carbon atom of the vinyl side chain on the carbonyl carbon atom are reported. Iminophosphorane 4 derived from ethyl β-azidoacrylate reacts with substituted cinnamyl aldehydes to give a mixture of 2-arylpyridine and 4-styryldihydropyridine derivatives, whereas the reaction with substituted benzaldehydes provides 4-aryldihydropyridine derivatives. However, the iminophosphorane 16 derived from the diethyl azidofumarate reacts with cinnamyl aldehydes through the expected aza-Wittig fashion to give 4-arylpyridine derivatives after dehydrogenation of the resulting dihydropyridine.
