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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

Mátyás Milen 1
Mátyás Milen
, 
Tímea Szabó 1
Tímea Szabó
, 
András Dancsó 1
András Dancsó
, 
Péter Ábrányi-Balogh 2
Péter Ábrányi-Balogh
, 
Balázs Volk 1
Balázs Volk
1 Egis Pharmaceuticals Plc., Directorate of Drug Substance Development, Budapest, Hungary
10.1016/j.mencom.2019.05.017
Published 2019-04-26
Communication , Volume 29, Issue 3, 294-295
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Milen M. et al. 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 Communications. 2019. Vol. 29. No. 3. pp. 294-295.
GOST all authors (up to 50) Copy
Milen M., Szabó T., Dancsó A., Ábrányi-Balogh P., Volk B. 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 Communications. 2019. Vol. 29. No. 3. pp. 294-295.
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TY - JOUR
DO - 10.1016/j.mencom.2019.05.017
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.05.017
TI - 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
T2 - Mendeleev Communications
AU - Milen, Mátyás
AU - Szabó, Tímea
AU - Dancsó, András
AU - Ábrányi-Balogh, Péter
AU - Volk, Balázs
PY - 2019
DA - 2019/04/26
PB - Mendeleev Communications
SP - 294-295
IS - 3
VL - 29
ER -
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@article{2019_Milen,
author = {Mátyás Milen and Tímea Szabó and András Dancsó and Péter Ábrányi-Balogh and Balázs Volk},
title = {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},
journal = {Mendeleev Communications},
year = {2019},
volume = {29},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.05.017},
number = {3},
pages = {294--295},
doi = {10.1016/j.mencom.2019.05.017}
}
MLA
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Milen, Mátyás, et al. “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 Communications, vol. 29, no. 3, Apr. 2019, pp. 294-295. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.05.017.

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.

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