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Novel 3,4-dihydro-1,4-oxazine (dehydromorpholine) sulfonamides and sulfones conveniently accessed from suitable a-diazoketones via O[sbnd]H carbene insertion – Cyclization sequence. / Solovyev, Igor; Dar'in, Dmitry; Krasavin, Mikhail.

в: Tetrahedron Letters, Том 78, № August, 153269, 17.08.2021.

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

Harvard

Solovyev, I, Dar'in, D & Krasavin, M 2021, 'Novel 3,4-dihydro-1,4-oxazine (dehydromorpholine) sulfonamides and sulfones conveniently accessed from suitable a-diazoketones via O[sbnd]H carbene insertion – Cyclization sequence', Tetrahedron Letters, Том. 78, № August, 153269. https://doi.org/10.1016/j.tetlet.2021.153269

APA

Solovyev, I., Dar'in, D., & Krasavin, M. (2021). Novel 3,4-dihydro-1,4-oxazine (dehydromorpholine) sulfonamides and sulfones conveniently accessed from suitable a-diazoketones via O[sbnd]H carbene insertion – Cyclization sequence. Tetrahedron Letters, 78(August), [153269]. https://doi.org/10.1016/j.tetlet.2021.153269

Vancouver

Solovyev I, Dar'in D, Krasavin M. Novel 3,4-dihydro-1,4-oxazine (dehydromorpholine) sulfonamides and sulfones conveniently accessed from suitable a-diazoketones via O[sbnd]H carbene insertion – Cyclization sequence. Tetrahedron Letters. 2021 Авг. 17;78(August). 153269. https://doi.org/10.1016/j.tetlet.2021.153269

Author

Solovyev, Igor ; Dar'in, Dmitry ; Krasavin, Mikhail. / Novel 3,4-dihydro-1,4-oxazine (dehydromorpholine) sulfonamides and sulfones conveniently accessed from suitable a-diazoketones via O[sbnd]H carbene insertion – Cyclization sequence. в: Tetrahedron Letters. 2021 ; Том 78, № August.

BibTeX

@article{aacdbdd7cfaf4b249e348f001f9ae5ef,
title = "Novel 3,4-dihydro-1,4-oxazine (dehydromorpholine) sulfonamides and sulfones conveniently accessed from suitable a-diazoketones via O[sbnd]H carbene insertion – Cyclization sequence",
abstract = "A short and practically convenient, modular approach to hitherto unknown dehydromorpholine sulfones and sulfonamides from α-acyl-α-diazomethyl sulfones and sulfonamides, respectively, has been developed. It involves Rh(II) carbene insertion into the O–H bond of 2-bromoethanol followed by thermally promoted tandem SN2 displacement of the bromine atom by a primary amine and cyclodehydration.",
keywords = "Alpha-Acyl-alpha-diazomethane sufones and solfamides, Dehydromorpholines, Privileged structures, Rh(II) carbene O-H insertion, Tandem SN2 – enamine formation, Tandem SN2-enamine formation",
author = "Igor Solovyev and Dmitry Dar'in and Mikhail Krasavin",
note = "Funding Information: This research was supported by the Russian Science Foundation (project grant 19-75-30008 ). Igor Solovyev is indebted to the Russian Foundation for Basic Research (project grant 19-33-90018) for the graduate student fellowship. We thank Research Centre for Magnetic Resonance and the Center for Chemical Analysis and Materials Research of Saint Petersburg State University Research Park for obtaining the analytical data. Publisher Copyright: {\textcopyright} 2021",
year = "2021",
month = aug,
day = "17",
doi = "10.1016/j.tetlet.2021.153269",
language = "English",
volume = "78",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier",
number = "August",

}

RIS

TY - JOUR

T1 - Novel 3,4-dihydro-1,4-oxazine (dehydromorpholine) sulfonamides and sulfones conveniently accessed from suitable a-diazoketones via O[sbnd]H carbene insertion – Cyclization sequence

AU - Solovyev, Igor

AU - Dar'in, Dmitry

AU - Krasavin, Mikhail

N1 - Funding Information: This research was supported by the Russian Science Foundation (project grant 19-75-30008 ). Igor Solovyev is indebted to the Russian Foundation for Basic Research (project grant 19-33-90018) for the graduate student fellowship. We thank Research Centre for Magnetic Resonance and the Center for Chemical Analysis and Materials Research of Saint Petersburg State University Research Park for obtaining the analytical data. Publisher Copyright: © 2021

PY - 2021/8/17

Y1 - 2021/8/17

N2 - A short and practically convenient, modular approach to hitherto unknown dehydromorpholine sulfones and sulfonamides from α-acyl-α-diazomethyl sulfones and sulfonamides, respectively, has been developed. It involves Rh(II) carbene insertion into the O–H bond of 2-bromoethanol followed by thermally promoted tandem SN2 displacement of the bromine atom by a primary amine and cyclodehydration.

AB - A short and practically convenient, modular approach to hitherto unknown dehydromorpholine sulfones and sulfonamides from α-acyl-α-diazomethyl sulfones and sulfonamides, respectively, has been developed. It involves Rh(II) carbene insertion into the O–H bond of 2-bromoethanol followed by thermally promoted tandem SN2 displacement of the bromine atom by a primary amine and cyclodehydration.

KW - Alpha-Acyl-alpha-diazomethane sufones and solfamides

KW - Dehydromorpholines

KW - Privileged structures

KW - Rh(II) carbene O-H insertion

KW - Tandem SN2 – enamine formation

KW - Tandem SN2-enamine formation

UR - http://www.scopus.com/inward/record.url?scp=85111591216&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/06cfe78f-882d-38c5-96ac-0468f5f64867/

U2 - 10.1016/j.tetlet.2021.153269

DO - 10.1016/j.tetlet.2021.153269

M3 - Article

AN - SCOPUS:85111591216

VL - 78

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - August

M1 - 153269

ER -

ID: 84591832