Russian Journal of Organic Chemistry, volume 55, issue 7, pages 1013-1018

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

Publication typeJournal Article
Publication date2019-07-01
Quartile SCImago
Q4
Quartile WOS
Q4
Impact factor0.8
ISSN10704280, 16083393
Organic Chemistry
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.

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Kobelev A. I. et al. Cleavage of Pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones with Thiocarbonohydrazide. Synthesis of Substituted 4-Amino-1,2,4-triazines // Russian Journal of Organic Chemistry. 2019. Vol. 55. No. 7. pp. 1013-1018.
GOST all authors (up to 50) Copy
Kobelev A. I., Stepanova E. E., Dmitriev M. V., Maslivets A. N. Cleavage of Pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones with Thiocarbonohydrazide. Synthesis of Substituted 4-Amino-1,2,4-triazines // Russian Journal of Organic Chemistry. 2019. Vol. 55. No. 7. pp. 1013-1018.
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TY - JOUR
DO - 10.1134/S1070428019070182
UR - https://doi.org/10.1134%2FS1070428019070182
TI - Cleavage of Pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones with Thiocarbonohydrazide. Synthesis of Substituted 4-Amino-1,2,4-triazines
T2 - Russian Journal of Organic Chemistry
AU - Kobelev, A I
AU - Stepanova, E E
AU - Dmitriev, M V
AU - Maslivets, A N
PY - 2019
DA - 2019/07/01 00:00:00
PB - Pleiades Publishing
SP - 1013-1018
IS - 7
VL - 55
SN - 1070-4280
SN - 1608-3393
ER -
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@article{2019_Kobelev
author = {A I Kobelev and E E Stepanova and M V Dmitriev and A N Maslivets},
title = {Cleavage of Pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones with Thiocarbonohydrazide. Synthesis of Substituted 4-Amino-1,2,4-triazines},
journal = {Russian Journal of Organic Chemistry},
year = {2019},
volume = {55},
publisher = {Pleiades Publishing},
month = {jul},
url = {https://doi.org/10.1134%2FS1070428019070182},
number = {7},
pages = {1013--1018},
doi = {10.1134/S1070428019070182}
}
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Kobelev, A. I., et al. “Cleavage of Pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones with Thiocarbonohydrazide. Synthesis of Substituted 4-Amino-1,2,4-triazines.” Russian Journal of Organic Chemistry, vol. 55, no. 7, Jul. 2019, pp. 1013-1018. https://doi.org/10.1134%2FS1070428019070182.
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