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Molecules 2015, 20(4), 5392-5408; doi:10.3390/molecules20045392

New 1-(3-Nitrophenyl)-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepines: Synthesis and Computational Study

1
Institute of Biochemistry, Vilnius University, Mokslininku 12, Vilnius LT-08662, Lithuania
2
Department of Technological Processes, Klaipeda University, H. Manto 84, Klaipeda LT-91001, Lithuania
3
Royal Institute of Technology, Department of Chemistry, Teknikringen 36, Stockholm S-10044, Sweden
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 6 January 2015 / Revised: 18 March 2015 / Accepted: 20 March 2015 / Published: 26 March 2015
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [1848 KB, uploaded 26 March 2015]   |  

Abstract

Triazole derivatives constitute an important group of heterocyclic compounds have have been the subject of extensive study in the recent past. These compounds have shown a wide range of biological and pharmacological activities. In this work, new fused tricyclic 1-(3-nitrophenyl)-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]-benzodiazepines have been synthesized by the thermal cyclization of N'-(2,3-dihydro-1H-1,5-benzodiazepin-4-yl)-3-nitrobenzohydrazides. After screening ethanol, toluene and 1-butanol as solvents, butanol-1 was found to be the best choice for the cyclization reaction in order to obtain the highest yields of tricyclic derivatives. The chemical structures of the synthesized compounds were elucidated by the analysis of their IR, 1H- and 13C-NMR spectral data. For tentative rationalization of the reaction processes, the global and local reactivity indices of certain compounds, taking part in the reaction pathway, were assessed by means of quantum mechanical calculations using the conceptual density functional theory (DFT) approach. This work could be useful for the synthesis of new heterocyclic compounds bearing a fused triazole ring. View Full-Text
Keywords: [1,2,4]triazolo[4,3-a][1,5]-benzodiazepine; 3-nitrobenzohydrazide; five-membered fused heterocycles; quantum mechanical calculation; density functional theory (DFT); DFT global descriptors; DFT local descriptors; Fukui index [1,2,4]triazolo[4,3-a][1,5]-benzodiazepine; 3-nitrobenzohydrazide; five-membered fused heterocycles; quantum mechanical calculation; density functional theory (DFT); DFT global descriptors; DFT local descriptors; Fukui index
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Kosychova, L.; Karalius, A.; Staniulytė, Z.; Sirutkaitis, R.A.; Palaima, A.; Laurynėnas, A.; Anusevičius, Ž. New 1-(3-Nitrophenyl)-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepines: Synthesis and Computational Study. Molecules 2015, 20, 5392-5408.

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