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Synthesis of Dibenzo[ d, f][1,3]Diazepines via Elemental Sulfur-Mediated Cyclocondensation of 2,2'-Biphenyldiamines with 2-Chloroacetic Acid Derivatives

Tatyana A Tikhonova, Konstantin A Lyssenko, Igor V Zavarzin, Yulia A Volkova

J Org Chem. 2019 Dec 20;84(24):15817-15826.

PMID: 31729874

Abstract:

The three-component reaction of 2,2'-biphenyldiamines with 2-chloroacetic acid derivatives and elemental sulfur was developed for the practical synthesis of unknown 2-carboxamide-substituted dibenzo[d,f][1,3]diazepines. This protocol is distinguished by efficiency in water and good tolerance to functional groups and can be adapted to a large-scale synthesis. The chemoselective preparation of a variety of 2-S,N,O-substituted dibenzo[d,f][1,3]diazepines was accomplished using the developed method.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP668983979 Dibenzo[b,d]thien-2-ylboronic acid Dibenzo[b,d]thien-2-ylboronic acid 668983-97-9 Price
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