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Rethinking Hydrolytic Imidazoline Ring Expansion : A Common Approach to the Preparation of Medium-Sized Rings via Side-Chain Insertion into [1.4]Oxa- and [1.4]Thiazepinone Scaffolds. / Reutskaya, Elena; Osipyan, Angelina; Sapegin, Alexander; Novikov, Alexander S.; Krasavin, Mikhail.

In: Journal of Organic Chemistry, Vol. 84, No. 4, 15.02.2019, p. 1693-1705.

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

Harvard

Reutskaya, E, Osipyan, A, Sapegin, A, Novikov, AS & Krasavin, M 2019, 'Rethinking Hydrolytic Imidazoline Ring Expansion: A Common Approach to the Preparation of Medium-Sized Rings via Side-Chain Insertion into [1.4]Oxa- and [1.4]Thiazepinone Scaffolds', Journal of Organic Chemistry, vol. 84, no. 4, pp. 1693-1705. https://doi.org/10.1021/acs.joc.8b02805

APA

Reutskaya, E., Osipyan, A., Sapegin, A., Novikov, A. S., & Krasavin, M. (2019). Rethinking Hydrolytic Imidazoline Ring Expansion: A Common Approach to the Preparation of Medium-Sized Rings via Side-Chain Insertion into [1.4]Oxa- and [1.4]Thiazepinone Scaffolds. Journal of Organic Chemistry, 84(4), 1693-1705. https://doi.org/10.1021/acs.joc.8b02805

Vancouver

Reutskaya E, Osipyan A, Sapegin A, Novikov AS, Krasavin M. Rethinking Hydrolytic Imidazoline Ring Expansion: A Common Approach to the Preparation of Medium-Sized Rings via Side-Chain Insertion into [1.4]Oxa- and [1.4]Thiazepinone Scaffolds. Journal of Organic Chemistry. 2019 Feb 15;84(4):1693-1705. https://doi.org/10.1021/acs.joc.8b02805

Author

Reutskaya, Elena ; Osipyan, Angelina ; Sapegin, Alexander ; Novikov, Alexander S. ; Krasavin, Mikhail. / Rethinking Hydrolytic Imidazoline Ring Expansion : A Common Approach to the Preparation of Medium-Sized Rings via Side-Chain Insertion into [1.4]Oxa- and [1.4]Thiazepinone Scaffolds. In: Journal of Organic Chemistry. 2019 ; Vol. 84, No. 4. pp. 1693-1705.

BibTeX

@article{1984966e94734094bf419f0da9245412,
title = "Rethinking Hydrolytic Imidazoline Ring Expansion: A Common Approach to the Preparation of Medium-Sized Rings via Side-Chain Insertion into [1.4]Oxa- and [1.4]Thiazepinone Scaffolds",
abstract = "The previously reported ring-expansion strategy involving hydrolytically prone imidazoline rings was thought to include the formation of a hydrated imidazoline intermediate. In this work, we accessed the latter via the addition of a 2-aminoethyl side chain onto a lactam moiety. This led to an efficient three-atom ring expansion of diarene-fused [1.4]oxazepines and [1.4]thiazepines and led us to propose to term this common approach the hydrated imidazoline ring expansion (HIRE) reaction. The strategy was extended to the insertion of longer (containing up to five atoms) side chains, and thus, larger (11- to 12-membered) diarene-fused rings were obtained via the homo-HIRE and homo2-HIRE reactions, respectively. This underscores the utility of the HIRE reaction for the preparation of medium-sized rings, an important class of chemical tools for interrogation of various biological targets.",
author = "Elena Reutskaya and Angelina Osipyan and Alexander Sapegin and Novikov, {Alexander S.} and Mikhail Krasavin",
note = "doi: 10.1021/acs.joc.8b02805",
year = "2019",
month = feb,
day = "15",
doi = "10.1021/acs.joc.8b02805",
language = "English",
volume = "84",
pages = "1693--1705",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "4",

}

RIS

TY - JOUR

T1 - Rethinking Hydrolytic Imidazoline Ring Expansion

T2 - A Common Approach to the Preparation of Medium-Sized Rings via Side-Chain Insertion into [1.4]Oxa- and [1.4]Thiazepinone Scaffolds

AU - Reutskaya, Elena

AU - Osipyan, Angelina

AU - Sapegin, Alexander

AU - Novikov, Alexander S.

AU - Krasavin, Mikhail

N1 - doi: 10.1021/acs.joc.8b02805

PY - 2019/2/15

Y1 - 2019/2/15

N2 - The previously reported ring-expansion strategy involving hydrolytically prone imidazoline rings was thought to include the formation of a hydrated imidazoline intermediate. In this work, we accessed the latter via the addition of a 2-aminoethyl side chain onto a lactam moiety. This led to an efficient three-atom ring expansion of diarene-fused [1.4]oxazepines and [1.4]thiazepines and led us to propose to term this common approach the hydrated imidazoline ring expansion (HIRE) reaction. The strategy was extended to the insertion of longer (containing up to five atoms) side chains, and thus, larger (11- to 12-membered) diarene-fused rings were obtained via the homo-HIRE and homo2-HIRE reactions, respectively. This underscores the utility of the HIRE reaction for the preparation of medium-sized rings, an important class of chemical tools for interrogation of various biological targets.

AB - The previously reported ring-expansion strategy involving hydrolytically prone imidazoline rings was thought to include the formation of a hydrated imidazoline intermediate. In this work, we accessed the latter via the addition of a 2-aminoethyl side chain onto a lactam moiety. This led to an efficient three-atom ring expansion of diarene-fused [1.4]oxazepines and [1.4]thiazepines and led us to propose to term this common approach the hydrated imidazoline ring expansion (HIRE) reaction. The strategy was extended to the insertion of longer (containing up to five atoms) side chains, and thus, larger (11- to 12-membered) diarene-fused rings were obtained via the homo-HIRE and homo2-HIRE reactions, respectively. This underscores the utility of the HIRE reaction for the preparation of medium-sized rings, an important class of chemical tools for interrogation of various biological targets.

UR - http://www.scopus.com/inward/record.url?scp=85061613470&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/rethinking-hydrolytic-imidazoline-ring-expansion-common-approach-preparation-mediumsized-rings-via-s

U2 - 10.1021/acs.joc.8b02805

DO - 10.1021/acs.joc.8b02805

M3 - Article

C2 - 30566355

VL - 84

SP - 1693

EP - 1705

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 4

ER -

ID: 37604151