Synthesis and intramolecular cyclization of N-acyl- and N-allyl-N'-(2-oxo-1,2-dihydro-pyridin-3-yl)thiourea

I. V. Kulakov; O. S. Nikitina; A. S. Fisyuk; D. S. Goncharov; Z. T. Shul'Gau; A. E. Gulyaev

doi:10.1007/s10593-014-1519-y

Synthesis and intramolecular cyclization of N-acyl- and N-allyl-N'-(2-oxo-1,2-dihydro-pyridin-3-yl)thiourea

I. V. Kulakov, O. S. Nikitina, A. S. Fisyuk, D. S. Goncharov, Z. T. Shul'Gau, A. E. Gulyaev

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Abstract

The reaction of 3-amino-4,6-dimethylpyridin-2(1H)-one and 3-amino-4-phenylpyridin-2-one with acyl isothiocyanates (benzoyl-, 4-bromobenzoyl-, and methacryloyl isothiocyanates) and with allyl isothiocyanate has been studied. The N-carbamothioyl methacrylamides and N-allylthioureas obtained undergo intramolecular heterocyclization reactions to give the corresponding 1,3-thiazin-4-one and 1,3-thiazoline derivatives. It was found that the starting 3-amino-4,6-dimethylpyridin-2(1H)-one shows antiradical activity but the synthesized thioureas do not.

Original language	English
Pages (from-to)	670-676
Number of pages	7
Journal	Chemistry of Heterocyclic Compounds
Volume	50
Issue number	5
DOIs	https://doi.org/10.1007/s10593-014-1519-y
Publication status	Published - Aug 2014

Keywords

1,3-thiazines
1,3-thiazolines
3-aminopyridin-2(1H)-ones
intramolecular cyclization
isothiocyanates
thioureas

ASJC Scopus subject areas

Organic Chemistry

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10.1007/s10593-014-1519-y

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@article{b06f76d21e8b4c9fa227b637479b8668,

title = "Synthesis and intramolecular cyclization of N-acyl- and N-allyl-N'-(2-oxo-1,2-dihydro-pyridin-3-yl)thiourea",

abstract = "The reaction of 3-amino-4,6-dimethylpyridin-2(1H)-one and 3-amino-4-phenylpyridin-2-one with acyl isothiocyanates (benzoyl-, 4-bromobenzoyl-, and methacryloyl isothiocyanates) and with allyl isothiocyanate has been studied. The N-carbamothioyl methacrylamides and N-allylthioureas obtained undergo intramolecular heterocyclization reactions to give the corresponding 1,3-thiazin-4-one and 1,3-thiazoline derivatives. It was found that the starting 3-amino-4,6-dimethylpyridin-2(1H)-one shows antiradical activity but the synthesized thioureas do not.",

keywords = "1,3-thiazines, 1,3-thiazolines, 3-aminopyridin-2(1H)-ones, intramolecular cyclization, isothiocyanates, thioureas",

author = "Kulakov, {I. V.} and Nikitina, {O. S.} and Fisyuk, {A. S.} and Goncharov, {D. S.} and Shul'Gau, {Z. T.} and Gulyaev, {A. E.}",

note = "Funding Information: This work was carried out with the financial support of the Russian Foundation for Basic Research (project 11-03-00338a).",

year = "2014",

month = aug,

doi = "10.1007/s10593-014-1519-y",

language = "English",

volume = "50",

pages = "670--676",

journal = "Chemistry of Heterocyclic Compounds",

issn = "0009-3122",

publisher = "Springer New York",

number = "5",

}

TY - JOUR

T1 - Synthesis and intramolecular cyclization of N-acyl- and N-allyl-N'-(2-oxo-1,2-dihydro-pyridin-3-yl)thiourea

AU - Kulakov, I. V.

AU - Nikitina, O. S.

AU - Fisyuk, A. S.

AU - Goncharov, D. S.

AU - Shul'Gau, Z. T.

AU - Gulyaev, A. E.

N1 - Funding Information: This work was carried out with the financial support of the Russian Foundation for Basic Research (project 11-03-00338a).

PY - 2014/8

Y1 - 2014/8

N2 - The reaction of 3-amino-4,6-dimethylpyridin-2(1H)-one and 3-amino-4-phenylpyridin-2-one with acyl isothiocyanates (benzoyl-, 4-bromobenzoyl-, and methacryloyl isothiocyanates) and with allyl isothiocyanate has been studied. The N-carbamothioyl methacrylamides and N-allylthioureas obtained undergo intramolecular heterocyclization reactions to give the corresponding 1,3-thiazin-4-one and 1,3-thiazoline derivatives. It was found that the starting 3-amino-4,6-dimethylpyridin-2(1H)-one shows antiradical activity but the synthesized thioureas do not.

AB - The reaction of 3-amino-4,6-dimethylpyridin-2(1H)-one and 3-amino-4-phenylpyridin-2-one with acyl isothiocyanates (benzoyl-, 4-bromobenzoyl-, and methacryloyl isothiocyanates) and with allyl isothiocyanate has been studied. The N-carbamothioyl methacrylamides and N-allylthioureas obtained undergo intramolecular heterocyclization reactions to give the corresponding 1,3-thiazin-4-one and 1,3-thiazoline derivatives. It was found that the starting 3-amino-4,6-dimethylpyridin-2(1H)-one shows antiradical activity but the synthesized thioureas do not.

KW - 1,3-thiazines

KW - 1,3-thiazolines

KW - 3-aminopyridin-2(1H)-ones

KW - intramolecular cyclization

KW - isothiocyanates

KW - thioureas

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U2 - 10.1007/s10593-014-1519-y

DO - 10.1007/s10593-014-1519-y

M3 - Article

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VL - 50

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EP - 676

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

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