Chemoselectivity of the 1,3-Dipolar Cycloaddition of Some Diazoalkanes with 1,5-Benzodiazepine Derivatives-Reference-Cited by-同舟云学术

Chemoselectivity of the 1,3-Dipolar Cycloaddition of Some Diazoalkanes with 1,5-Benzodiazepine Derivatives

Published:2012-03 Issue:3 Volume:36 Page:152-156
ISSN:1747-5198
Container-title:Journal of Chemical Research
language:en
Short-container-title:Journal of Chemical Research

Author:

Nsira Asma¹,Karoui Ahlem²,Gharbi Rafik²,Msaddek Moncef¹

Affiliation:

1. Laboratoire de Synthèse Hétérocyclique et Substances Naturelles Faculté des Sciences, Monastir, Tunisia

2. Ecole Préparatoire aux Académies Militaires, Sousse, Tunisia

Abstract

Benzodiazepines are pharmaceutically important synthetic materials. Reaction of the 4-(2-hydroxyphenyl)-1,5-benzodiazepin-2-one with 2-diazopropane (DAP) gave a mixture of the 2-isopropylether of 4-(2-hydroxyphenyl)-3H-1,5-benzodiazepine and 1-isopropyl-4-(2-hydroxyphenyl)-3H-1,5-benzodiazepin-2-one. Whilst diphenyldiazomethane (DPDM) gave 1-benzhydryl-4-(2-hydroxyphenyl)-3H-1,5-benzodiazepin-2-one. Reaction of the corresponding thione with DAP led to the 2-isopropylthioether of 4-(2-hydroxyphenyl)-3H-1,5-benzodiazepine and 1-isopropyl-4-(2-hydroxyphenyl)-1,5-benzodiazepine-2-thione while the reaction with DPDM gave the 2-benzhydrylthioether of 4-(2-hydroxyphenyl)-3H-1,5-benzodiazepine. The characterisation of these prepared - N, - O and - S alkylated benzodiazepines involved 1D and 2D-NMR techniques, mass spectrometry and elemental analysis.

Publisher

SAGE Publications

Subject

General Chemistry

Link

http://journals.sagepub.com/doi/pdf/10.3184/174751912X13300109535030

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