Reaction of Diethyl Chloroethynylphosphonate with 3-Amino-1,2,4-triazoles

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Reaction of Diethyl Chloroethynylphosphonate with 3-Amino-1,2,4-triazoles. / Krylov, A. S.; Tolstyakov, V. V.; Gurzhiy, V. V.; Dogadina, A. V.

In: Russian Journal of General Chemistry, Vol. 91, No. 1, 12.02.2021, p. 72-76.

Research output: Contribution to journal › Article › peer-review

Author

Krylov, A. S. ; Tolstyakov, V. V. ; Gurzhiy, V. V. ; Dogadina, A. V. / Reaction of Diethyl Chloroethynylphosphonate with 3-Amino-1,2,4-triazoles. In: Russian Journal of General Chemistry. 2021 ; Vol. 91, No. 1. pp. 72-76.

BibTeX

@article{7172fe29fb714eacadd239c5607a8b42,

title = "Reaction of Diethyl Chloroethynylphosphonate with 3-Amino-1,2,4-triazoles",

abstract = "A series of new 6-phosphonylated 1H-imidazo[2,1-c][1,2,4]triazoles was synthesized by the reaction of diethyl chloroethynylphosphonate with 2-substituted 3-amino-1,2,4-triazoles followed by 5-endo-dig cyclization. It was found that 3-amino-5-bromo-1,2,4-triazole reacts in another way, leading to the formation of the corresponding symmetric amidine, diethyl {2-[(3-bromo-1-methyl-1H-1,2,4-triazol-5-yl)amino]-2-[(3-bromo-1-methyl-1H-1,2,4-triazol-5-yl)imino]ethyl}phosphonate.",

keywords = "3-amino-1,2,4-triazole, chloroethynylphosphonate, imidazotriazole, phosphorylation, 2, 4-triazole, 3-amino-1",

author = "Krylov, {A. S.} and Tolstyakov, {V. V.} and Gurzhiy, {V. V.} and Dogadina, {A. V.}",

note = "Funding Information: This work was financially supported by the Ministry of Science and Higher Education of the Russian Federation (project no. 785.00.X6019) and the Russian Foundation for Basic Research (grant no. 19-03-00365) using the equipment of the Engineering Center of the St. Petersburg State Institute of Technology, and Resource Centers “Center for X-Ray Diffraction Studies” and “Chemical Analysis and Materials Research Center” of the Research Park of St. Petersburg State University. Publisher Copyright: {\textcopyright} 2021, Pleiades Publishing, Ltd. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.",

year = "2021",

month = feb,

day = "12",

doi = "10.1134/s1070363221010072",

language = "English",

volume = "91",

pages = "72--76",

journal = "Russian Journal of General Chemistry",

issn = "1070-3632",

publisher = "МАИК {"}Наука/Интерпериодика{"}",

number = "1",

}

RIS

TY - JOUR

T1 - Reaction of Diethyl Chloroethynylphosphonate with 3-Amino-1,2,4-triazoles

AU - Krylov, A. S.

AU - Tolstyakov, V. V.

AU - Gurzhiy, V. V.

AU - Dogadina, A. V.

N1 - Funding Information: This work was financially supported by the Ministry of Science and Higher Education of the Russian Federation (project no. 785.00.X6019) and the Russian Foundation for Basic Research (grant no. 19-03-00365) using the equipment of the Engineering Center of the St. Petersburg State Institute of Technology, and Resource Centers “Center for X-Ray Diffraction Studies” and “Chemical Analysis and Materials Research Center” of the Research Park of St. Petersburg State University. Publisher Copyright: © 2021, Pleiades Publishing, Ltd. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.

PY - 2021/2/12

Y1 - 2021/2/12

N2 - A series of new 6-phosphonylated 1H-imidazo[2,1-c][1,2,4]triazoles was synthesized by the reaction of diethyl chloroethynylphosphonate with 2-substituted 3-amino-1,2,4-triazoles followed by 5-endo-dig cyclization. It was found that 3-amino-5-bromo-1,2,4-triazole reacts in another way, leading to the formation of the corresponding symmetric amidine, diethyl {2-[(3-bromo-1-methyl-1H-1,2,4-triazol-5-yl)amino]-2-[(3-bromo-1-methyl-1H-1,2,4-triazol-5-yl)imino]ethyl}phosphonate.

AB - A series of new 6-phosphonylated 1H-imidazo[2,1-c][1,2,4]triazoles was synthesized by the reaction of diethyl chloroethynylphosphonate with 2-substituted 3-amino-1,2,4-triazoles followed by 5-endo-dig cyclization. It was found that 3-amino-5-bromo-1,2,4-triazole reacts in another way, leading to the formation of the corresponding symmetric amidine, diethyl {2-[(3-bromo-1-methyl-1H-1,2,4-triazol-5-yl)amino]-2-[(3-bromo-1-methyl-1H-1,2,4-triazol-5-yl)imino]ethyl}phosphonate.

KW - 3-amino-1,2,4-triazole

KW - chloroethynylphosphonate

KW - imidazotriazole

KW - phosphorylation

KW - 2

KW - 4-triazole

KW - 3-amino-1

UR - http://www.scopus.com/inward/record.url?scp=85100861647&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/e44221d1-aab0-3525-a49f-2ba9d82c7c80/

U2 - 10.1134/s1070363221010072

DO - 10.1134/s1070363221010072

M3 - Article

AN - SCOPUS:85100861647

VL - 91

SP - 72

EP - 76

JO - Russian Journal of General Chemistry

JF - Russian Journal of General Chemistry

SN - 1070-3632

IS - 1

ER -

ID: 74670580