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

Molecules

Lidija Kosychova¹  Antanas Karalius²  Zita Staniulytė¹  Romualdas Aleksas Sirutkaitis¹  Algirdas Palaima¹  Audrius Laurynėnas¹  Žilvinas Anusevičius¹ 

[1] Institute of Biochemistry, Vilnius University, Mokslininku 12, Vilnius LT-08662, Lithuania; E-Mails:;Royal Institute of Technology, Department of Chemistry, Teknikringen 36, Stockholm S-10044, Sweden; E-Mail:

关键词: [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;   

DOI  :  10.3390/molecules20045392

来源: mdpi

【 摘 要 】

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.

【 授权许可】

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© 2015 by the authors; licensee MDPI, Basel, Switzerland.