Organic Letters

, том 11 , издание 4 , страницы 979-982

Dibenzoxazepinium ylides: Facile access and 1,3-dipolar cycloaddition reactions

Тип публикации: Journal Article

Дата публикации: 2009-01-13

American Chemical Society (ACS)

Organic Letters

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wos Q1

БС1

SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/ol802813a

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PubMed ID: 19140740

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Краткое описание

An effective approach to azirino-fused heterocycles is disclosed. The approach, involving formation of heterocycle/C-(arylchloromethyl)-subsituted CN double bond via domino isomerization of a gem-dichloroaziridine-intramolecular Friedel-Crafts acylation of the O-tethered benzene ring and subsequent intramolecular cyclization induced by hydride, was realized for 1-aryl-1,11b-dihydroazirino[1,2-d]dibenz[b,f][1,4]oxazepines. The latter are excellent precursors of azomethine ylides, especially in solvent-free conditions, which can undergo a completely stereoselective 1,3-dipolar cycloaddition to CC dipolarophiles giving derivatives of dibenzo[b,f]pyrrolo[1,2-d][1,4]oxazepine.

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Новиков Михаил

д.х.н., доц.

219 публикаций, 4 258 цитирований, 54 рецензии

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Санкт-Петербургский государственный университет

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Khlebnikov A. F. et al. Dibenzoxazepinium ylides: Facile access and 1,3-dipolar cycloaddition reactions // Organic Letters. 2009. Vol. 11. No. 4. pp. 979-982.

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Khlebnikov A. F., Novikov M. S., Petrovskii P. P., Magull J., Ringe A. Dibenzoxazepinium ylides: Facile access and 1,3-dipolar cycloaddition reactions // Organic Letters. 2009. Vol. 11. No. 4. pp. 979-982.

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TY - JOUR

DO - 10.1021/ol802813a

UR - https://doi.org/10.1021/ol802813a

TI - Dibenzoxazepinium ylides: Facile access and 1,3-dipolar cycloaddition reactions

T2 - Organic Letters

AU - Khlebnikov, Alexander F

AU - Novikov, Mikhail S.

AU - Petrovskii, Petr P

AU - Magull, Joerg

AU - Ringe, Arne

PY - 2009

DA - 2009/01/13

PB - American Chemical Society (ACS)

SP - 979-982

IS - 4

VL - 11

PMID - 19140740

SN - 1523-7060

SN - 1523-7052

ER -

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@article{2009_Khlebnikov,

author = {Alexander F Khlebnikov and Mikhail S. Novikov and Petr P Petrovskii and Joerg Magull and Arne Ringe},

title = {Dibenzoxazepinium ylides: Facile access and 1,3-dipolar cycloaddition reactions},

journal = {Organic Letters},

year = {2009},

volume = {11},

publisher = {American Chemical Society (ACS)},

month = {jan},

url = {https://doi.org/10.1021/ol802813a},

number = {4},

pages = {979--982},

doi = {10.1021/ol802813a}

}

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Khlebnikov, Alexander F., et al. “Dibenzoxazepinium ylides: Facile access and 1,3-dipolar cycloaddition reactions.” Organic Letters, vol. 11, no. 4, Jan. 2009, pp. 979-982. https://doi.org/10.1021/ol802813a.