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Synthesis of 1,2-Dihydropyrimidine-2-carboxylates via Regioselective Addition of Rhodium(II) Carbenoids to 2H-Azirine-2-carbaldimines. / Novikov, Mikhail S.; Rostovskii, Nikolai V.; Koronatov, Alexander N.; Zavyalov, Kirill V.; Zubakin, Grigory V.; Khlebnikov, Alexander F.; Starova, Galina L.

In: Journal of Organic Chemistry, Vol. 82, No. 24, 15.12.2017, p. 13396-13404.

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

Harvard

Novikov, MS, Rostovskii, NV, Koronatov, AN, Zavyalov, KV, Zubakin, GV, Khlebnikov, AF & Starova, GL 2017, 'Synthesis of 1,2-Dihydropyrimidine-2-carboxylates via Regioselective Addition of Rhodium(II) Carbenoids to 2H-Azirine-2-carbaldimines', Journal of Organic Chemistry, vol. 82, no. 24, pp. 13396-13404. https://doi.org/10.1021/acs.joc.7b02484

APA

Novikov, M. S., Rostovskii, N. V., Koronatov, A. N., Zavyalov, K. V., Zubakin, G. V., Khlebnikov, A. F., & Starova, G. L. (2017). Synthesis of 1,2-Dihydropyrimidine-2-carboxylates via Regioselective Addition of Rhodium(II) Carbenoids to 2H-Azirine-2-carbaldimines. Journal of Organic Chemistry, 82(24), 13396-13404. https://doi.org/10.1021/acs.joc.7b02484

Vancouver

Novikov MS, Rostovskii NV, Koronatov AN, Zavyalov KV, Zubakin GV, Khlebnikov AF et al. Synthesis of 1,2-Dihydropyrimidine-2-carboxylates via Regioselective Addition of Rhodium(II) Carbenoids to 2H-Azirine-2-carbaldimines. Journal of Organic Chemistry. 2017 Dec 15;82(24):13396-13404. https://doi.org/10.1021/acs.joc.7b02484

Author

Novikov, Mikhail S. ; Rostovskii, Nikolai V. ; Koronatov, Alexander N. ; Zavyalov, Kirill V. ; Zubakin, Grigory V. ; Khlebnikov, Alexander F. ; Starova, Galina L. / Synthesis of 1,2-Dihydropyrimidine-2-carboxylates via Regioselective Addition of Rhodium(II) Carbenoids to 2H-Azirine-2-carbaldimines. In: Journal of Organic Chemistry. 2017 ; Vol. 82, No. 24. pp. 13396-13404.

BibTeX

@article{4d394c8ad5d9499ca6e884dc13ac6e08,
title = "Synthesis of 1,2-Dihydropyrimidine-2-carboxylates via Regioselective Addition of Rhodium(II) Carbenoids to 2H-Azirine-2-carbaldimines",
abstract = "An efficient two-step procedure {"}imine formation/azirine-carbenoid coupling{"} has been developed for the preparation of 1,2-dihydropyrimidines from azirine-2-carbaldehydes, primary amines, and diazo carbonyl compounds under Rh(II) catalysis. The formation of 1,2-dihydropyrimidines involves 100% regioselective addition of the rhodium carbenoid to endocyclic nitrogen atom of the 2H-azirine-2-carbaldimine. According to the DFT calculations the reaction proceeds via dissociation of the metal-bound complex of the azirinium ylide to metal-free azirinium ylide, ring-opening of the latter to give a 1,5-diazahexa-1,3,5-triene, followed by 1,6-cyclization. The 1,2-dihydropyrimidines with two different electron-withdrawing substituents at the C2 position can undergo in solution inversion of configuration of the stereogenic center at C2 via {"}the N1-C2 bond cleavage/rotation around the N-C single bond/1,6-cyclization{"} sequence.",
author = "Novikov, {Mikhail S.} and Rostovskii, {Nikolai V.} and Koronatov, {Alexander N.} and Zavyalov, {Kirill V.} and Zubakin, {Grigory V.} and Khlebnikov, {Alexander F.} and Starova, {Galina L.}",
year = "2017",
month = dec,
day = "15",
doi = "10.1021/acs.joc.7b02484",
language = "English",
volume = "82",
pages = "13396--13404",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "24",

}

RIS

TY - JOUR

T1 - Synthesis of 1,2-Dihydropyrimidine-2-carboxylates via Regioselective Addition of Rhodium(II) Carbenoids to 2H-Azirine-2-carbaldimines

AU - Novikov, Mikhail S.

AU - Rostovskii, Nikolai V.

AU - Koronatov, Alexander N.

AU - Zavyalov, Kirill V.

AU - Zubakin, Grigory V.

AU - Khlebnikov, Alexander F.

AU - Starova, Galina L.

PY - 2017/12/15

Y1 - 2017/12/15

N2 - An efficient two-step procedure "imine formation/azirine-carbenoid coupling" has been developed for the preparation of 1,2-dihydropyrimidines from azirine-2-carbaldehydes, primary amines, and diazo carbonyl compounds under Rh(II) catalysis. The formation of 1,2-dihydropyrimidines involves 100% regioselective addition of the rhodium carbenoid to endocyclic nitrogen atom of the 2H-azirine-2-carbaldimine. According to the DFT calculations the reaction proceeds via dissociation of the metal-bound complex of the azirinium ylide to metal-free azirinium ylide, ring-opening of the latter to give a 1,5-diazahexa-1,3,5-triene, followed by 1,6-cyclization. The 1,2-dihydropyrimidines with two different electron-withdrawing substituents at the C2 position can undergo in solution inversion of configuration of the stereogenic center at C2 via "the N1-C2 bond cleavage/rotation around the N-C single bond/1,6-cyclization" sequence.

AB - An efficient two-step procedure "imine formation/azirine-carbenoid coupling" has been developed for the preparation of 1,2-dihydropyrimidines from azirine-2-carbaldehydes, primary amines, and diazo carbonyl compounds under Rh(II) catalysis. The formation of 1,2-dihydropyrimidines involves 100% regioselective addition of the rhodium carbenoid to endocyclic nitrogen atom of the 2H-azirine-2-carbaldimine. According to the DFT calculations the reaction proceeds via dissociation of the metal-bound complex of the azirinium ylide to metal-free azirinium ylide, ring-opening of the latter to give a 1,5-diazahexa-1,3,5-triene, followed by 1,6-cyclization. The 1,2-dihydropyrimidines with two different electron-withdrawing substituents at the C2 position can undergo in solution inversion of configuration of the stereogenic center at C2 via "the N1-C2 bond cleavage/rotation around the N-C single bond/1,6-cyclization" sequence.

UR - http://www.scopus.com/inward/record.url?scp=85038431000&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.7b02484

DO - 10.1021/acs.joc.7b02484

M3 - Article

AN - SCOPUS:85038431000

VL - 82

SP - 13396

EP - 13404

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 24

ER -

ID: 13392547