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

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.

Key words

1,5-benzodiazepine - 1,4-dihydropyridine - fused-ring systems - trifluoroacetic acid - chirality

• References

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