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Unexpected Ring Contraction of Homophthalic Anhydrides under Diazo Transfer Conditions. / Kazantsev, Alexander; Bakulina, Olga; Dar'in, Dmitry; Kantin, Grigory; Bunev, Alexander; Krasavin, Mikhail.

In: Organic Letters, Vol. 24, No. 26, 08.07.2022, p. 4762-4765.

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

Harvard

Kazantsev, A, Bakulina, O, Dar'in, D, Kantin, G, Bunev, A & Krasavin, M 2022, 'Unexpected Ring Contraction of Homophthalic Anhydrides under Diazo Transfer Conditions', Organic Letters, vol. 24, no. 26, pp. 4762-4765. https://doi.org/10.1021/acs.orglett.2c01730, https://doi.org/10.1021/acs.orglett.2c01730

APA

Kazantsev, A., Bakulina, O., Dar'in, D., Kantin, G., Bunev, A., & Krasavin, M. (2022). Unexpected Ring Contraction of Homophthalic Anhydrides under Diazo Transfer Conditions. Organic Letters, 24(26), 4762-4765. https://doi.org/10.1021/acs.orglett.2c01730, https://doi.org/10.1021/acs.orglett.2c01730

Vancouver

Kazantsev A, Bakulina O, Dar'in D, Kantin G, Bunev A, Krasavin M. Unexpected Ring Contraction of Homophthalic Anhydrides under Diazo Transfer Conditions. Organic Letters. 2022 Jul 8;24(26):4762-4765. https://doi.org/10.1021/acs.orglett.2c01730, https://doi.org/10.1021/acs.orglett.2c01730

Author

Kazantsev, Alexander ; Bakulina, Olga ; Dar'in, Dmitry ; Kantin, Grigory ; Bunev, Alexander ; Krasavin, Mikhail. / Unexpected Ring Contraction of Homophthalic Anhydrides under Diazo Transfer Conditions. In: Organic Letters. 2022 ; Vol. 24, No. 26. pp. 4762-4765.

BibTeX

@article{6ca7d6e088074dcfaac1849caf3e55b5,
title = "Unexpected Ring Contraction of Homophthalic Anhydrides under Diazo Transfer Conditions",
abstract = "An attempted Regitz diazo transfer onto homophthalic anhydride led to the discovery of an unexpected ring contraction, which gave N-sulfonyl phthalide-3-carboxamide derivatives. The reaction is thought to proceed via a [3 + 2] cycloaddition of the substrate's enol form and the azide followed by a two-step fragmentation of the intermediate 1,2,3-triazoline with a loss of the nitrogen molecule.",
author = "Alexander Kazantsev and Olga Bakulina and Dmitry Dar'in and Grigory Kantin and Alexander Bunev and Mikhail Krasavin",
note = "Publisher Copyright: {\textcopyright} 2022 American Chemical Society.",
year = "2022",
month = jul,
day = "8",
doi = "10.1021/acs.orglett.2c01730",
language = "English",
volume = "24",
pages = "4762--4765",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "26",

}

RIS

TY - JOUR

T1 - Unexpected Ring Contraction of Homophthalic Anhydrides under Diazo Transfer Conditions

AU - Kazantsev, Alexander

AU - Bakulina, Olga

AU - Dar'in, Dmitry

AU - Kantin, Grigory

AU - Bunev, Alexander

AU - Krasavin, Mikhail

N1 - Publisher Copyright: © 2022 American Chemical Society.

PY - 2022/7/8

Y1 - 2022/7/8

N2 - An attempted Regitz diazo transfer onto homophthalic anhydride led to the discovery of an unexpected ring contraction, which gave N-sulfonyl phthalide-3-carboxamide derivatives. The reaction is thought to proceed via a [3 + 2] cycloaddition of the substrate's enol form and the azide followed by a two-step fragmentation of the intermediate 1,2,3-triazoline with a loss of the nitrogen molecule.

AB - An attempted Regitz diazo transfer onto homophthalic anhydride led to the discovery of an unexpected ring contraction, which gave N-sulfonyl phthalide-3-carboxamide derivatives. The reaction is thought to proceed via a [3 + 2] cycloaddition of the substrate's enol form and the azide followed by a two-step fragmentation of the intermediate 1,2,3-triazoline with a loss of the nitrogen molecule.

UR - http://www.scopus.com/inward/record.url?scp=85134361177&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.2c01730

DO - 10.1021/acs.orglett.2c01730

M3 - Article

C2 - 35749721

AN - SCOPUS:85134361177

VL - 24

SP - 4762

EP - 4765

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 26

ER -

ID: 97337539