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Russian Journal of Organic Chemistry

, Volume 55, Issue 7, pp 1013–1018 | Cite as

Cleavage of Pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones with Thiocarbonohydrazide. Synthesis of Substituted 4-Amino-1,2,4-triazines

  • A. I. Kobelev
  • E. E. Stepanova
  • M. V. Dmitriev
  • A. N. MaslivetsEmail author
Article
  • 23 Downloads

Abstract

3-Acylpyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones reacted with thiocarbonohydrazide to give mixtures of 4-amino-6-(acylmethyl)-3-sulfanylidene-3,4-dihydro-1,2,4-triazin-5(2H)-ones and 6-substituted 1,4-benzoxazine-2,3-diones which can be separated by fractional crystallization directly from the reaction mixture. The reaction is likely to involve a sequence of nucleophilic transformations with intermediate formation of spiro[pyrrole-2,6′-[1,2,4]triazines] which undergo cleavage of the C2-N1 bond in the pyrrole ring. The structure of the products was determined by X-ray analysis, and intermediate products were identified by UPLC/MS. 1,2,4-Triazine derivatives can also be synthesized independently from alkyl 2,4-dioxobutanoates or 2-oxobutanedioic acid and thiocarbonohydrazide. The known procedure for the synthesis of 4-amino-1,2,4-triazines from 4-aryl-2,4-dioxobutanoic acids and thiocarbonohydrazide was improved to meet the “green chemistry” principles. Two new methods for the synthesis of substituted 4-amino-1,2,4-triazines were developed. The obtained compounds attract interest for medicinal chemistry, pharmacology, and fine organic synthesis.

Keywords

1H-pyrrole-2,3-diones hetareno[e]pyrrole-2,3-diones pyrrolobenzoxazinetriones thiocarbonohydrazide 1,2,4-triazines 1,4-benzoxazine X-ray analysis 2,4-dioxobutanoic acid esters divergent synthesis green chemistry 

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Notes

Funding

This study was performed under financial support by the Ministry of Science and Higher Education of the Russian Federation (project no. 4.6774.2017/8.9) and by the Government of Perm Krai.

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Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • A. I. Kobelev
    • 1
  • E. E. Stepanova
    • 1
  • M. V. Dmitriev
    • 1
  • A. N. Maslivets
    • 1
    Email author
  1. 1.Perm State UniversityPermRussia

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