M. Milen, T. Szabó, A. Dancsó, P. Ábrányi-Balogh, B. Volk, “Synthesis of 1-aryl-3H-[1,2,5]triazepino[5,4-a]benzimidazol-4(5H)-ones and quantum chemical investigation of the rotamers of the Boc-protected hydrazide key intermediate”, Mendeleev Commun., 2019, Volume 29, Issue 3,Pages 294

Communications

Synthesis of 1-aryl-3H-[1,2,5]triazepino[5,4-a]benzimidazol-4(5H)-ones and quantum chemical investigation of the rotamers of the Boc-protected hydrazide key intermediate

M. Milen^a, T. Szabó^a, A. Dancsó^a, P. Ábrányi-Balogh^b, B. Volk^a

^a Egis Pharmaceuticals Plc., Directorate of Drug Substance Development, Budapest, Hungary
^b Research Centre for Natural Sciences, Hungarian Academy of Sciences, Budapest, Hungary

Abstract: 3H-[1,2,5]Triazepino[5,4-a]benzimidazol-4(5H)-ones were obtained in five steps involving C-acylation of benzimidazole, its N-alkylation with ethyl bromoacetate, the ester hydrolysis, condensation with BocNHNH₂, and the acid-catalyzed heterocyclization of thus obtained 2-(2-aroyl-1H-benzimidazol-1-yl)-N′-(tert-butoxycarbonyl)acetohydrazides. The geometry of tert-butyl carbazate rotamers was estimated with quantum chemical calculations.

Language: English

DOI: 10.1016/j.mencom.2019.05.017

	*Supplementary materials:*
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