Acyl derivatives of 3-amino-1,2,4-triazole

Zh N. Fidler; E. F. Shibanova; P. V. Makerov; I. D. Kalikhman; A. M. Shulunova; G. I. Sarapulova; L. V. Klyba; V. Yu Vitkovskii; N. N. Chipanina; V. A. Lopyrev; M. G. Voronkov

doi:10.1007/BF00496616

Acyl derivatives of 3-amino-1,2,4-triazole

Zh N. Fidler, E. F. Shibanova, P. V. Makerov, I. D. Kalikhman, A. M. Shulunova, G. I. Sarapulova, L. V. Klyba, V. Yu Vitkovskii, N. N. Chipanina, V. A. Lopyrev, M. G. Voronkov

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Abstract

Only 3-acylamino-1,2,4-triazoles were isolated in the acylation of 3-amino-1,2,4-triazole with acid chlorides that contain strong electron acceptor substituents. Acylation takes place in the 2 position when aliphatic and aromatic acid chlorides are used as the acylating agents. The action of methoxy- and ethoxyformyl chlorides leads to the formation of 1- and 2-alkoxycarbonyl-3-amino-1,2,4-triazoles. When N-acyl-3-amino-1,2,4-triazoles are heated, they undergo intermolecular trans-aminoacylation to 3-acylamino-1,2,4-triazoles, which exist in the solid phase in the form of amido and imido tautomers. Under the conditions of massspectroscopic analysis the percentage of the imido form increases as the electronacceptor capacity of the substituent increases.

Original language	English
Pages (from-to)	1079-1083
Number of pages	5
Journal	Chemistry of Heterocyclic Compounds
Volume	16
Issue number	10
DOIs	https://doi.org/10.1007/BF00496616
State	Published - 1 Oct 1980
Externally published	Yes

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Organic Chemistry

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title = "Acyl derivatives of 3-amino-1,2,4-triazole",

abstract = "Only 3-acylamino-1,2,4-triazoles were isolated in the acylation of 3-amino-1,2,4-triazole with acid chlorides that contain strong electron acceptor substituents. Acylation takes place in the 2 position when aliphatic and aromatic acid chlorides are used as the acylating agents. The action of methoxy- and ethoxyformyl chlorides leads to the formation of 1- and 2-alkoxycarbonyl-3-amino-1,2,4-triazoles. When N-acyl-3-amino-1,2,4-triazoles are heated, they undergo intermolecular trans-aminoacylation to 3-acylamino-1,2,4-triazoles, which exist in the solid phase in the form of amido and imido tautomers. Under the conditions of massspectroscopic analysis the percentage of the imido form increases as the electronacceptor capacity of the substituent increases.",

author = "Fidler, {Zh N.} and Shibanova, {E. F.} and Makerov, {P. V.} and Kalikhman, {I. D.} and Shulunova, {A. M.} and Sarapulova, {G. I.} and Klyba, {L. V.} and Vitkovskii, {V. Yu} and Chipanina, {N. N.} and Lopyrev, {V. A.} and Voronkov, {M. G.}",

year = "1980",

month = oct,

day = "1",

doi = "10.1007/BF00496616",

language = "English",

volume = "16",

pages = "1079--1083",

journal = "Chemistry of Heterocyclic Compounds",

issn = "0009-3122",

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TY - JOUR

T1 - Acyl derivatives of 3-amino-1,2,4-triazole

AU - Fidler, Zh N.

AU - Shibanova, E. F.

AU - Makerov, P. V.

AU - Kalikhman, I. D.

AU - Shulunova, A. M.

AU - Sarapulova, G. I.

AU - Klyba, L. V.

AU - Vitkovskii, V. Yu

AU - Chipanina, N. N.

AU - Lopyrev, V. A.

AU - Voronkov, M. G.

PY - 1980/10/1

Y1 - 1980/10/1

N2 - Only 3-acylamino-1,2,4-triazoles were isolated in the acylation of 3-amino-1,2,4-triazole with acid chlorides that contain strong electron acceptor substituents. Acylation takes place in the 2 position when aliphatic and aromatic acid chlorides are used as the acylating agents. The action of methoxy- and ethoxyformyl chlorides leads to the formation of 1- and 2-alkoxycarbonyl-3-amino-1,2,4-triazoles. When N-acyl-3-amino-1,2,4-triazoles are heated, they undergo intermolecular trans-aminoacylation to 3-acylamino-1,2,4-triazoles, which exist in the solid phase in the form of amido and imido tautomers. Under the conditions of massspectroscopic analysis the percentage of the imido form increases as the electronacceptor capacity of the substituent increases.

AB - Only 3-acylamino-1,2,4-triazoles were isolated in the acylation of 3-amino-1,2,4-triazole with acid chlorides that contain strong electron acceptor substituents. Acylation takes place in the 2 position when aliphatic and aromatic acid chlorides are used as the acylating agents. The action of methoxy- and ethoxyformyl chlorides leads to the formation of 1- and 2-alkoxycarbonyl-3-amino-1,2,4-triazoles. When N-acyl-3-amino-1,2,4-triazoles are heated, they undergo intermolecular trans-aminoacylation to 3-acylamino-1,2,4-triazoles, which exist in the solid phase in the form of amido and imido tautomers. Under the conditions of massspectroscopic analysis the percentage of the imido form increases as the electronacceptor capacity of the substituent increases.

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DO - 10.1007/BF00496616

M3 - Article

AN - SCOPUS:18344394835

SN - 0009-3122

VL - 16

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EP - 1083

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

IS - 10

ER -

Acyl derivatives of 3-amino-1,2,4-triazole

Abstract

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