Organic Letters

, volume 11 , issue 4 , pages 979-982

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

Alexander F Khlebnikov ¹

Mikhail S. Novikov ¹

Petr P Petrovskii ¹

Joerg Magull ¹

Arne Ringe ¹

Hide authors affiliations Show authors affiliations: 1 affiliation

Department of Chemistry, St. Petersburg State University, Universitetskii pr. 26, 198504 St. Petersburg, Russia, and Institute of Inorganic Chemistry of Georg-August-University, Göttingen, Germany |

Publication type: Journal Article

Publication date: 2009-01-13

American Chemical Society (ACS)

Organic Letters

scimago Q1

wos Q1

SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/ol802813a

Copy DOI

PubMed ID: 19140740

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

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.

Found

7 citations

Novikov Mikhail

DSc in Chemistry, associate professor

216 publications, 4 151 citations, 54 reviews

h-index: 33

Saint Petersburg State University

Top-30

Journals

	1 2 3 4 5 6
Journal of Organic Chemistry	Journal of Organic Chemistry, 6, 17.14% Journal of Organic Chemistry 6 publications, 17.14%
Organic Letters	Organic Letters, 4, 11.43% Organic Letters 4 publications, 11.43%
Chemistry of Heterocyclic Compounds	Chemistry of Heterocyclic Compounds, 3, 8.57% Chemistry of Heterocyclic Compounds 3 publications, 8.57%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 3, 8.57% Organic and Biomolecular Chemistry 3 publications, 8.57%
European Journal of Organic Chemistry	European Journal of Organic Chemistry, 3, 8.57% European Journal of Organic Chemistry 3 publications, 8.57%
Tetrahedron Letters	Tetrahedron Letters, 2, 5.71% Tetrahedron Letters 2 publications, 5.71%
Chemical Communications	Chemical Communications, 2, 5.71% Chemical Communications 2 publications, 5.71%
Molecular Diversity	Molecular Diversity, 1, 2.86% Molecular Diversity 1 publication, 2.86%
Tetrahedron	Tetrahedron, 1, 2.86% Tetrahedron 1 publication, 2.86%
ChemCatChem	ChemCatChem, 1, 2.86% ChemCatChem 1 publication, 2.86%
ChemistrySelect	ChemistrySelect, 1, 2.86% ChemistrySelect 1 publication, 2.86%
ChemInform	ChemInform, 1, 2.86% ChemInform 1 publication, 2.86%
Chemistry - A European Journal	Chemistry - A European Journal, 1, 2.86% Chemistry - A European Journal 1 publication, 2.86%
RSC Advances	RSC Advances, 1, 2.86% RSC Advances 1 publication, 2.86%
New Journal of Chemistry	New Journal of Chemistry, 1, 2.86% New Journal of Chemistry 1 publication, 2.86%
Russian Journal of Organic Chemistry	Russian Journal of Organic Chemistry, 1, 2.86% Russian Journal of Organic Chemistry 1 publication, 2.86%
Progress in Heterocyclic Chemistry	Progress in Heterocyclic Chemistry, 1, 2.86% Progress in Heterocyclic Chemistry 1 publication, 2.86%
Organic Reaction Mechanisms	Organic Reaction Mechanisms, 1, 2.86% Organic Reaction Mechanisms 1 publication, 2.86%
	1 2 3 4 5 6

Publishers

	2 4 6 8 10
American Chemical Society (ACS)	American Chemical Society (ACS), 10, 28.57% American Chemical Society (ACS) 10 publications, 28.57%
Wiley	Wiley, 8, 22.86% Wiley 8 publications, 22.86%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 7, 20% Royal Society of Chemistry (RSC) 7 publications, 20%
Elsevier	Elsevier, 5, 14.29% Elsevier 5 publications, 14.29%
Springer Nature	Springer Nature, 4, 11.43% Springer Nature 4 publications, 11.43%
Pleiades Publishing	Pleiades Publishing, 1, 2.86% Pleiades Publishing 1 publication, 2.86%
	2 4 6 8 10

We do not take into account publications without a DOI.
Statistics recalculated weekly.

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.

Metrics

Cite this

GOST |

Cite this

GOST Copy

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.

GOST all authors (up to 50) Copy

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.

RIS |

Cite this

RIS Copy

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 -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@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}

}

MLA

Cite this

MLA Copy

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.