Journal of Heterocyclic Chemistry

, volume 50 , issue 2 , pages 326-336

Reaction of 1,2-dialkyldiaziridines and 1,2,3-trialkyldiaziridines with methyl propiolate in ionic liquids and in organic solvents

Vera Yu. Petukhova ^{1, 2}

Leonid L. Fershtat ¹

Vadim V. Kachala ^{1, 2}

V. V. Kuznetsov ¹

Vladimir V. Kuznetsov ²

Dmitriy V Khakimov ^{1, 2}

Tatyana S Pivina ¹

Nina N. Makhova ¹

Hide authors affiliations Show authors affiliations: 2 affiliations

N. D. Zelinsky Institute of Organic Chemistry; Russian Academy of Sciences; Moscow 119991; Russian Federation |

N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences Moscow 119991 Russian Federation |

Publication type: Journal Article

Publication date: 2013-03-01

Wiley

Journal of Heterocyclic Chemistry

scimago Q3

wos Q2

SJR: 0.362

CiteScore: 4.7

Impact factor: 2.4

ISSN: 0022152X, 19435193

DOI: 10.1002/jhet.1079

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Organic Chemistry

Abstract

An interaction of 1,2‐dialkyldiaziridine and 1,2,3‐trialkyldiaziridine with methyl propiolate was studied both in organic solvent (MeCN, CH₂Cl₂, C₆H₆) and in ionic liquids. Earlier unknown linear structures, in which three molecules of methyl propiolate were suited to one diaziridine molecule (adducts 1 : 3), were obtained in MeCN. The diaziridine ring expansion products 1,2,3,4‐tetrahydropyrimidine derivatives (adducts 1 : 2) and, along with them in some cases, the same linear structures were obtained in ionic liquids. A mechanism of reactions found was offered. The regioselectivity of reactions was supposed to determine by the structure of substituents in initial diaziridines. This conclusion was supported by quantum chemical calculations.

Found

4 citations

Fershtat Leonid

DSc in Chemistry

146 publications, 2 959 citations, 121 reviews

h-index: 29

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

4 citations

Kulikov Aleksandr

PhD in Chemistry

62 publications, 1 008 citations

h-index: 19

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

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Petukhova V. Y. et al. Reaction of 1,2-dialkyldiaziridines and 1,2,3-trialkyldiaziridines with methyl propiolate in ionic liquids and in organic solvents // Journal of Heterocyclic Chemistry. 2013. Vol. 50. No. 2. pp. 326-336.

GOST all authors (up to 50) Copy

Petukhova V. Y., Fershtat L. L., Kachala V. V., Kuznetsov V. V., Kuznetsov V. V., Khakimov D. V., Pivina T. S., Makhova N. N. Reaction of 1,2-dialkyldiaziridines and 1,2,3-trialkyldiaziridines with methyl propiolate in ionic liquids and in organic solvents // Journal of Heterocyclic Chemistry. 2013. Vol. 50. No. 2. pp. 326-336.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1002/jhet.1079

UR - https://onlinelibrary.wiley.com/doi/10.1002/jhet.1079

TI - Reaction of 1,2-dialkyldiaziridines and 1,2,3-trialkyldiaziridines with methyl propiolate in ionic liquids and in organic solvents

T2 - Journal of Heterocyclic Chemistry

AU - Petukhova, Vera Yu.

AU - Fershtat, Leonid L.

AU - Kachala, Vadim V.

AU - Kuznetsov, V. V.

AU - Kuznetsov, Vladimir V.

AU - Khakimov, Dmitriy V

AU - Pivina, Tatyana S

AU - Makhova, Nina N.

PY - 2013

DA - 2013/03/01

PB - Wiley

SP - 326-336

IS - 2

VL - 50

SN - 0022-152X

SN - 1943-5193

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2013_Petukhova,

author = {Vera Yu. Petukhova and Leonid L. Fershtat and Vadim V. Kachala and V. V. Kuznetsov and Vladimir V. Kuznetsov and Dmitriy V Khakimov and Tatyana S Pivina and Nina N. Makhova},

title = {Reaction of 1,2-dialkyldiaziridines and 1,2,3-trialkyldiaziridines with methyl propiolate in ionic liquids and in organic solvents},

journal = {Journal of Heterocyclic Chemistry},

year = {2013},

volume = {50},

publisher = {Wiley},

month = {mar},

url = {https://onlinelibrary.wiley.com/doi/10.1002/jhet.1079},

number = {2},

pages = {326--336},

doi = {10.1002/jhet.1079}

}

MLA

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MLA Copy

Petukhova, Vera Yu., et al. “Reaction of 1,2-dialkyldiaziridines and 1,2,3-trialkyldiaziridines with methyl propiolate in ionic liquids and in organic solvents.” Journal of Heterocyclic Chemistry, vol. 50, no. 2, Mar. 2013, pp. 326-336. https://onlinelibrary.wiley.com/doi/10.1002/jhet.1079.