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

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

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2019, Volume: 84, Number: 24, Pages: 15817-15826 Pages count : 10 DOI: 10.1021/acs.joc.9b02002

Authors

Tikhonova Tatyana A. ¹ , Lyssenko Konstantin A. ^2,3 , Zavarzin Igor V. ¹ , Volkova Yulia A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., Moscow 119991, Russia
2	Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow 119991, Russia
3	Plekhanov Russian University of Economics, Stremyanny per. 36, Moscow 117997, Russia

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.

Tikhonova T.A. , Lyssenko K.A. , Zavarzin I.V. , Volkova Y.A.
Synthesis of Dibenzo[d,f][1,3]Diazepines via Elemental Sulfur-Mediated Cyclocondensation of 2,2′-Biphenyldiamines with 2-Chloroacetic Acid Derivatives
Journal of Organic Chemistry. 2019. V.84. N24. P.15817-15826. DOI: 10.1021/acs.joc.9b02002 WOS Scopus OpenAlex

≡ Web of science:	WOS:000504805700006
≡ Scopus:	2-s2.0-85076254083
≡ OpenAlex:	W2986237975