Issue 11, 2003
From the journal:

New Journal of Chemistry

1,3-Dipolar cycloaddition of nitrilimines to 2,4-disubstituted-3H-1,5-benzodiazepines: remarkable effect of C4-substituent on diastereoselectivity

Khadija Nabih,a   Abdesselam Baouid,*a   Aissa Hasnaoui,a   Mohamed Selktib  and  Philippe Compain*c  

* Corresponding authors

a Laboratoire de Chimie des Substances Naturelles et des Hétérocycles, département de chimie, Faculté des Sciences-Semlalia, B.P. 2390, Université Cadi Ayyad, Marrakech, Morocco
E-mail: baouid.abdesselam@caramail.com

b Laboratoire de Cristallographie et RMN Biologiques, UMR 8015 CNRS-Faculté de Pharmacie, 4 avenue de l'Observatoire, Paris cedex 6, France

c Institut de Chimie Organique et Analytique (CNRS UMR 6005), Rue de Chartres, BP 6759, Orléans cedex 2, France
E-mail: philippe.compain@univ-orleans.fr

Abstract

The one-step synthesis of new bis[1,2,4-triazolo][4,3-a:3′,4′-d][1,5] benzodiazepines by way of completely regio- and diastereoselective 1,3-dipolar cycloaddition of nitrilimines to 2,4-dimethyl-3H-1,5-benzodiazepines is reported and a tentative rationalization for the observed diastereoselectivity, which underline the key effect of the C4-dipolarophile substituent, is proposed.

Graphical abstract: 1,3-Dipolar cycloaddition of nitrilimines to 2,4-disubstituted-3H-1,5-benzodiazepines: remarkable effect of C4-substituent on diastereoselectivity

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Article information

DOI
https://doi.org/10.1039/B303995C
Article type
Paper
Submitted
09 Apr 2003
Accepted
03 Jun 2003
First published
05 Sep 2003

New J. Chem., 2003,27, 1644-1648

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1,3-Dipolar cycloaddition of nitrilimines to 2,4-disubstituted-3H-1,5-benzodiazepines: remarkable effect of C4-substituent on diastereoselectivity

K. Nabih, A. Baouid, A. Hasnaoui, M. Selkti and P. Compain, New J. Chem., 2003, 27, 1644 DOI: 10.1039/B303995C

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