Cycloaddition of benzynes and nitrile oxides: synthesis of benzisoxazoles

被引：29

作者：

Crossley, James A. ^{[1
]}

Browne, Duncan L. ^{[1
]}

机构：

[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 17期

基金：

英国工程与自然科学研究理事会;

关键词：

CONCISE TOTAL-SYNTHESIS; CATALYZED ALKYNE-ARYNE; COUPLING REACTIONS; CLICK CHEMISTRY; ANNULATION; BENZOTRIAZOLES; PYRIDINES; AZIDES;

D O I：

10.1016/j.tetlet.2010.02.103

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and efficient process has been developed for the synthesis of benzisoxazoles through the cycloaddition of benzynes and nitrile oxides. This method allows access to both (hetero)aromatic and alkenyl-substituted benzisoxazoles. Preliminary studies concerning regioselectivity are also reported. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：2271 / 2273

页数：3

共 31 条

[1] Copper-catalyzed alkyne-aryne coupling reaction under microwave conditions: preparation of unsymmetric and symmetric di-substituted alkynes [J].

Akubathini, Shashidhar Kumar ;

Biehl, Ed .

TETRAHEDRON LETTERS, 2009, 50 (16) :1809-1811

[2] A Concise Total Synthesis of (-)-Quinocarcin via Aryne Annulation [J].

Allan, Kevin M. ;

Stoltz, Brian M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (51) :17270-+

[3] Regioselective Diels-Alder cycloadditions and other reactions of 4,5-, 5,6-, and 6,7-indole arynes [J].

Brown, Neil ;

Luo, Diheng ;

Velde, David Vander ;

Yang, Shaorong ;

Brassfield, Allen ;

Buszek, Keith R. .

TETRAHEDRON LETTERS, 2009, 50 (01) :63-65

[4] A smooth access to benzotriazoles via azide-benzyne cycloaddition [J].

Chandrasekhar, S. ;

Seenaiah, M. ;

Rao, Ch. Lohitha ;

Reddy, Ch. Raji .

TETRAHEDRON, 2008, 64 (49) :11325-11327

[5] A novel α,β-unsaturated nitrone-aryne [3+2] cycloaddition and its application in the synthesis of the cortistatin core [J].

Dai, Mingji ;

Wang, Zhang ;

Danishefsky, Samuel J. .

TETRAHEDRON LETTERS, 2008, 49 (47) :6613-6616

[6] Orthogonal synthesis of indolines and isoquinolines via aryne annulation [J].

Gilmore, Christopher D. ;

Allan, Kevin M. ;

Stoltz, Brian M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (05) :1558-+

[7] NITRILE OXIDES .11. DIMERIZATION OF A STERICALLY HINDERED NITRILE OXIDE . DIMESITYLFURAZAN OXIDE [J].

GRUNDMAN.C ;

FROMMELD, HD ;

FLORY, K ;

DATTA, SK .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (04) :1464-&

[8]

Grundmann C., 1970, SYNTHESIS, V7, P344, DOI DOI 10.1055/S-1970-21611

[9] Intramolecular [4+2] cycloadditions of benzynes with conjugated enynes, arenynes, and dienes [J].

Hayes, ME ;

Shinokubo, H ;

Danheiser, RL .

ORGANIC LETTERS, 2005, 7 (18) :3917-3920

[10] Biaryl synthesis via palladium-catalyzed aryne multicomponent coupling [J].

Henderson, Jaclyn L. ;

Edwards, Andrew S. ;

Greaney, Michael F. .

ORGANIC LETTERS, 2007, 9 (26) :5589-5592

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