Synthesis 2016; 48(09): 1414-1420
DOI: 10.1055/s-0035-1560409
paper
© Georg Thieme Verlag Stuttgart · New York

A Highly Efficient Synthesis of Optically Active Hybrid 1H-1,5-Benzodiazepine–1,4-Dihydropyridines

Susana Y. Torres
,
Francisca Rebolledo*
Further Information

Publication History

Received: 07 December 2015

Accepted after revision: 14 January 2016

Publication Date:
17 February 2016 (online)


Abstract

A series of optically active hybrid compounds, 4-aryl-3-(ethoxycarbonyl)-2-methyl-4,11-dihydro-1H-benzo[b]pyrido[2,3-e][1,4]di­azepin-6-ium salts, containing the 1H-1,5-benzodiazepine and 1,4-dihydropyridine units have been effectively synthesized by means of a coupling reaction between enantioenriched 6-chloro-5-formyl-1,4-dihydropyridine derivatives and benzene-1,2-diamine. The use of trifluoroacetic acid allowed the corresponding hybrids to be obtained in very high yields. No racemization took place in the processes.

Supporting Information

 
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