Transformations of 1,2,4-triazines in reactions with nucleophiles: V. SNH and ipso-substitution in the synthesis and transformations of 5-cyano-1,2,4-triazines

D. N. Kozhevnikov; V. N. Kozhevnikov; I. S. Kovalev; V. L. Rusinov; O. N. Chupakhin; G. G. Aleksandrov

doi:10.1023/A:1019631610505

Transformations of 1,2,4-triazines in reactions with nucleophiles: V. S_N^H and ipso-substitution in the synthesis and transformations of 5-cyano-1,2,4-triazines

D. N. Kozhevnikov, V. N. Kozhevnikov, I. S. Kovalev, V. L. Rusinov, O. N. Chupakhin, G. G. Aleksandrov

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

43 Citations (Scopus)

Abstract

The scope of functionalization of 1,2,4-triazines can be considerably extended via successive nucleophilic substitution of hydrogen (S _N^H) and ipso-substitution. A convenient procedure has been developed for direct cyanation of 1,2,4-triazine 4-oxides with acetone cyanohydrin in the presence of triethylamine. The cyano group in the resulting 5-cyano-1,2,4-triazines is readily replaced by reactions with various aliphatic alcohols and amines.

Original language	English
Pages (from-to)	744-750
Number of pages	7
Journal	Russian Journal of Organic Chemistry
Volume	38
Issue number	5
DOIs	https://doi.org/10.1023/A:1019631610505
Publication status	Published - May 2002
Externally published	Yes

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Kozhevnikov, D. N., Kozhevnikov, V. N., Kovalev, I. S., Rusinov, V. L., Chupakhin, O. N., & Aleksandrov, G. G. (2002). Transformations of 1,2,4-triazines in reactions with nucleophiles: V. S_N^H and ipso-substitution in the synthesis and transformations of 5-cyano-1,2,4-triazines. Russian Journal of Organic Chemistry, 38(5), 744-750. https://doi.org/10.1023/A:1019631610505

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title = "Transformations of 1,2,4-triazines in reactions with nucleophiles: V. SNH and ipso-substitution in the synthesis and transformations of 5-cyano-1,2,4-triazines",

abstract = "The scope of functionalization of 1,2,4-triazines can be considerably extended via successive nucleophilic substitution of hydrogen (S NH) and ipso-substitution. A convenient procedure has been developed for direct cyanation of 1,2,4-triazine 4-oxides with acetone cyanohydrin in the presence of triethylamine. The cyano group in the resulting 5-cyano-1,2,4-triazines is readily replaced by reactions with various aliphatic alcohols and amines.",

author = "Kozhevnikov, \{D. N.\} and Kozhevnikov, \{V. N.\} and Kovalev, \{I. S.\} and Rusinov, \{V. L.\} and Chupakhin, \{O. N.\} and Aleksandrov, \{G. G.\}",

year = "2002",

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doi = "10.1023/A:1019631610505",

language = "English",

volume = "38",

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Transformations of 1,2,4-triazines in reactions with nucleophiles: V. S_N^H and ipso-substitution in the synthesis and transformations of 5-cyano-1,2,4-triazines. / Kozhevnikov, D. N.; Kozhevnikov, V. N.; Kovalev, I. S. et al.
In: Russian Journal of Organic Chemistry, Vol. 38, No. 5, 05.2002, p. 744-750.

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

TY - JOUR

T1 - Transformations of 1,2,4-triazines in reactions with nucleophiles

T2 - V. SNH and ipso-substitution in the synthesis and transformations of 5-cyano-1,2,4-triazines

AU - Kozhevnikov, D. N.

AU - Kozhevnikov, V. N.

AU - Kovalev, I. S.

AU - Rusinov, V. L.

AU - Chupakhin, O. N.

AU - Aleksandrov, G. G.

PY - 2002/5

Y1 - 2002/5

N2 - The scope of functionalization of 1,2,4-triazines can be considerably extended via successive nucleophilic substitution of hydrogen (S NH) and ipso-substitution. A convenient procedure has been developed for direct cyanation of 1,2,4-triazine 4-oxides with acetone cyanohydrin in the presence of triethylamine. The cyano group in the resulting 5-cyano-1,2,4-triazines is readily replaced by reactions with various aliphatic alcohols and amines.

AB - The scope of functionalization of 1,2,4-triazines can be considerably extended via successive nucleophilic substitution of hydrogen (S NH) and ipso-substitution. A convenient procedure has been developed for direct cyanation of 1,2,4-triazine 4-oxides with acetone cyanohydrin in the presence of triethylamine. The cyano group in the resulting 5-cyano-1,2,4-triazines is readily replaced by reactions with various aliphatic alcohols and amines.

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DO - 10.1023/A:1019631610505

M3 - Article

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JO - Russian Journal of Organic Chemistry

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IS - 5

ER -

Transformations of 1,2,4-triazines in reactions with nucleophiles: V. SNH and ipso-substitution in the synthesis and transformations of 5-cyano-1,2,4-triazines

Abstract

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Transformations of 1,2,4-triazines in reactions with nucleophiles: V. S_N^H and ipso-substitution in the synthesis and transformations of 5-cyano-1,2,4-triazines