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Synthesis 2012(4): 591-599  
DOI: 10.1055/s-0031-1289670
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Rapid Synthesis of Benzodiazepines by Ring Expansion of Aziridines with Anthranilic Acids by Using a Grinding Technique

Atul K. Singh, Lal Dhar S. Yadav*
Green Synthesis Lab, Department of Chemistry, University of Allahabad, Allahabad 211 002, India
Fax: +91(532)2460533; e-Mail: ldsyadav@hotmail.com;
Further Information

Publication History

Received 11 September 2011
Publication Date:
16 January 2012 (online)

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Abstract

A grinding-induced, atom-economic, rapid, efficient, one-pot protocol was developed for the synthesis of pharmaceutically relevant benzo-1,4-diazepin-5-ones in excellent yields (72-91%) and high regioselectivities. The method involves a ring-opening­-ring-closure cascade of aziridines with anthranilic acids by grinding the neat reactants at room temperature in the presence of lithium bromide as a mild catalyst. Among the advantages of this protocol are its economic viability, the ability to recycle the catalyst, and the formation of water as the only byproduct.

Key words

heterocycles - cyclizations - solid-phase synthesis - cascade reactions - benzodiazepines

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