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An Alternative Approach to the Hydrated Imidazoline Ring Expansion (HIRE) of Diarene-Fused [1.4]Oxazepines. / Grintsevich, Sergey; Sapegin, Alexander; Reutskaya, Elena; Peintner, Stefan; Erdélyi, Máté; Krasavin, Mikhail.

в: European Journal of Organic Chemistry, Том 2020, № 35, 22.09.2020, стр. 5664-5676.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

Harvard

Grintsevich, S, Sapegin, A, Reutskaya, E, Peintner, S, Erdélyi, M & Krasavin, M 2020, 'An Alternative Approach to the Hydrated Imidazoline Ring Expansion (HIRE) of Diarene-Fused [1.4]Oxazepines', European Journal of Organic Chemistry, Том. 2020, № 35, стр. 5664-5676. https://doi.org/10.1002/ejoc.202000789

APA

Grintsevich, S., Sapegin, A., Reutskaya, E., Peintner, S., Erdélyi, M., & Krasavin, M. (2020). An Alternative Approach to the Hydrated Imidazoline Ring Expansion (HIRE) of Diarene-Fused [1.4]Oxazepines. European Journal of Organic Chemistry, 2020(35), 5664-5676. https://doi.org/10.1002/ejoc.202000789

Vancouver

Grintsevich S, Sapegin A, Reutskaya E, Peintner S, Erdélyi M, Krasavin M. An Alternative Approach to the Hydrated Imidazoline Ring Expansion (HIRE) of Diarene-Fused [1.4]Oxazepines. European Journal of Organic Chemistry. 2020 Сент. 22;2020(35):5664-5676. https://doi.org/10.1002/ejoc.202000789

Author

Grintsevich, Sergey ; Sapegin, Alexander ; Reutskaya, Elena ; Peintner, Stefan ; Erdélyi, Máté ; Krasavin, Mikhail. / An Alternative Approach to the Hydrated Imidazoline Ring Expansion (HIRE) of Diarene-Fused [1.4]Oxazepines. в: European Journal of Organic Chemistry. 2020 ; Том 2020, № 35. стр. 5664-5676.

BibTeX

@article{b7f38b6dd9d844339535ff6e30cb8e5d,
title = "An Alternative Approach to the Hydrated Imidazoline Ring Expansion (HIRE) of Diarene-Fused [1.4]Oxazepines",
abstract = "A four-step approach to the “hydrated imidazoline ring expansion” (HIRE) is presented. In most cases, the ring expansion was the sole process. However, for the first time, an alternative course of the hydrated imidazoline evolution was discovered which gave N-aminoethyl derivatives. These can, in principle, be converted into the target HIRE products under sufficiently forcing conditions. The approach offers improved flexibility with respect to the peripheral substituents and is also applicable to the synthesis of eleven-membered lactams. We observed that the latter can exist in two stable isomeric forms due to lactam–amide bond isomerization. The latter finding further demonstrates the value of medium-sized rings as multiple-conformer probes for biological target interrogation.",
keywords = "Amide bond isomerism, Hydrogen bonds, Imidazolinium salts, Medium-sized rings, Ring expansion, PERMEABILITY, AMIDINES, NATURAL-PRODUCTS, DRUGS, LACTAMS",
author = "Sergey Grintsevich and Alexander Sapegin and Elena Reutskaya and Stefan Peintner and M{\'a}t{\'e} Erd{\'e}lyi and Mikhail Krasavin",
year = "2020",
month = sep,
day = "22",
doi = "10.1002/ejoc.202000789",
language = "English",
volume = "2020",
pages = "5664--5676",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-Blackwell",
number = "35",

}

RIS

TY - JOUR

T1 - An Alternative Approach to the Hydrated Imidazoline Ring Expansion (HIRE) of Diarene-Fused [1.4]Oxazepines

AU - Grintsevich, Sergey

AU - Sapegin, Alexander

AU - Reutskaya, Elena

AU - Peintner, Stefan

AU - Erdélyi, Máté

AU - Krasavin, Mikhail

PY - 2020/9/22

Y1 - 2020/9/22

N2 - A four-step approach to the “hydrated imidazoline ring expansion” (HIRE) is presented. In most cases, the ring expansion was the sole process. However, for the first time, an alternative course of the hydrated imidazoline evolution was discovered which gave N-aminoethyl derivatives. These can, in principle, be converted into the target HIRE products under sufficiently forcing conditions. The approach offers improved flexibility with respect to the peripheral substituents and is also applicable to the synthesis of eleven-membered lactams. We observed that the latter can exist in two stable isomeric forms due to lactam–amide bond isomerization. The latter finding further demonstrates the value of medium-sized rings as multiple-conformer probes for biological target interrogation.

AB - A four-step approach to the “hydrated imidazoline ring expansion” (HIRE) is presented. In most cases, the ring expansion was the sole process. However, for the first time, an alternative course of the hydrated imidazoline evolution was discovered which gave N-aminoethyl derivatives. These can, in principle, be converted into the target HIRE products under sufficiently forcing conditions. The approach offers improved flexibility with respect to the peripheral substituents and is also applicable to the synthesis of eleven-membered lactams. We observed that the latter can exist in two stable isomeric forms due to lactam–amide bond isomerization. The latter finding further demonstrates the value of medium-sized rings as multiple-conformer probes for biological target interrogation.

KW - Amide bond isomerism

KW - Hydrogen bonds

KW - Imidazolinium salts

KW - Medium-sized rings

KW - Ring expansion

KW - PERMEABILITY

KW - AMIDINES

KW - NATURAL-PRODUCTS

KW - DRUGS

KW - LACTAMS

UR - http://www.scopus.com/inward/record.url?scp=85088018900&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/1cd33088-65ff-306d-90c7-186a5ca9394d/

U2 - 10.1002/ejoc.202000789

DO - 10.1002/ejoc.202000789

M3 - Article

AN - SCOPUS:85088018900

VL - 2020

SP - 5664

EP - 5676

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 35

ER -

ID: 60838312