Unusual Reactivity of (Vinylimino)phosphoranes and Their Utility in the Preparation of Pyridine and Dihydropyridine Derivatives

Autor:	M. J. Vilaplana, Pedro Molina, and Aurelia Pastor
Rok vydání:	1996
Předmět:	Carbon atom Organic Chemistry Dihydropyridine Medicinal chemistry chemistry.chemical_compound chemistry Nucleophile Pyridine medicine Side chain Dehydrogenation Reactivity (chemistry) Dihydropyridine derivatives medicine.drug
Zdroj:	The Journal of Organic Chemistry. 61:8094-8098
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo960940v
Popis:	New reactions of (vinylimino)phosphoranes with aldehydes involving an initial nucleophilic attack of the beta-carbon atom of the vinyl side chain on the carbonyl carbon atom are reported. Iminophosphorane 4 derived from ethyl beta-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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::4e2eab63b9b66d05300f54b88c8c8940 https://doi.org/10.1021/jo960940v Zobrazit plný text záznamu