The synthesis of derivatives of tetra(hexa)hydro[1,2,3]triazolo-[4,5-e][1,4]diazepines and their acylation

Authors

  • N. O. Syrota National University of Kyiv-Mohyla Academy, Ukraine
  • S. V. Kemskiy Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • A. V. Bol’but Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • I. I. Chornobaev Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • V. V. Vovk Institute of Organic Chemistry of the NAS of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.18.952

Keywords:

derivatives of [1, 2, 3] triazolo [4, 5-e][1, 4] diazepines, selective reduction, complex hydrides of metals, acylation

Abstract

Aim. To study the conditions for reduction of 5-hydroxy[1,2,3]triazolo[4,5-e][1,4]diazepines and develop the method for the synthesis of their tetra- and hexahydroderivatives.

Results and discussion. It has been found that the functional hydroxy and carbonyl groups of 5-hydroxy[1,2,3]triazolo[4,5-e][1,4]diazepines tend to selective reduction with complex metal hydrides, and it has allowed to develop methods for the synthesis of their hydrogenated derivatives and to carry out the acylation of the diazepine cycle.

Experimental part. The selective reduction of the hydroxy group was obtained by the interaction of 5-hydroxy[1,2,3]triazolo[4,5-e][1,4]diazepines with a 2-fold excess of NaBH4 in the boiling isopropanol. It allowed obtaining derivatives of tetrahydro[1,2,3]triazolo[4,5-e][1,4]diazepine-8(3H)-one with the yield of 61-82 %. The complete reduction of the diazepine cycle can be achieved only by using a 5-fold excess of LiAlH4-Me3SiCl hydration system and long-term boiling in THF. It has been shown that the tetrahydroderivatives synthesized with aliphatic carboxylic anhydrides are prone to selective acylation of the N4 diazepine ring atom, while hexahydroderivatives form a product of acetylation at N4 and N6 atoms.

Conclusions. The conditions for the partial and complete reduction of 5-hydroxy[1,2,3]triazolo[4,5-e][1,4]diazepines have been found, convenient methods for the synthesis of tetrahydro- and hexahydroderivatives have been developed, and their directed functionalization by acyl groups has been performed.

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Published

2018-12-14

How to Cite

(1)
Syrota, N. O.; Kemskiy, S. V.; Bol’but, A. V.; Chornobaev, I. I.; Vovk, V. V. The Synthesis of Derivatives of tetra(hexa)hydro[1,2,3]triazolo-[4,5-e][1,4]diazepines and Their Acylation. J. Org. Pharm. Chem. 2018, 16, 28-33.

Issue

Vol. 16 No. 4(64) (2018)

Section

Original Researches

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