An Efficient One Pot Protocol to the Annulation of Face “d” of Benzazepinone Ring with Pyrazole, Isoxazole, and Pyrimidine Nucleus through the Corresponding Oxoketene Dithioacetal DerivativeReportar como inadecuado




An Efficient One Pot Protocol to the Annulation of Face “d” of Benzazepinone Ring with Pyrazole, Isoxazole, and Pyrimidine Nucleus through the Corresponding Oxoketene Dithioacetal Derivative - Descarga este documento en PDF. Documentación en PDF para descargar gratis. Disponible también para leer online.

Advances in ChemistryVolume 2014 2014, Article ID 358153, 5 pages

Research ArticleDepartment of Chemistry, Banasthali University, Banasthali, Raj 304022, India

Received 5 April 2014; Accepted 16 July 2014; Published 6 August 2014

Academic Editor: Manuel Sergi

Copyright © 2014 Aditi Anand et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

A highly facile single step approach to the annulation of face “d” of benzazepinone nucleus with pyrazole, isoxazole, and pyrimidine ring has been described. The annulation proceeded smoothly on the reaction of oxoketene dithioacetal derivative 3 with i NH2–NH2·H2O, ii NH2OH·HCl, iii acetamidine hydrochloride, iv guanidine nitrate, v urea, and vi thiourea which yielded the pyrazolo, isoxazolo, and pyrimido annulated analogues of benzazepinone 4–9, respectively, in acceptable yields. The 4-ketene dithioacetal analogue of 7-fluorobenzobazepine-2,5-dione 3 was in turn obtained from the reaction of 7-fluoro-3,4-dihydro-1H-benzobazepine-2,5-dione 2 with CS2 + CH3I in presence of t-BuOK. 7-Fluoro-3,4-dihydro-1H-benzobazepine-2,5-dione 2 resulted from the acylation of p-fluoroaniline with succinyl chloride followed by cyclocondensation of the later with polyphosphoric acid PPA.





Autor: Aditi Anand, Navjeet Kaur, and Dharma Kishore

Fuente: https://www.hindawi.com/



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