An improved synthesis of 1,2-benzisoxazoles: TBAF mediated 1,3-dipolar cycloaddition of nitrile oxides and benzyne

被引：52

作者：

Spiteri, Christian ^{[1
,2
]}

Sharma, Pallavi ^{[1
,2
]}

Zhang, Fengzhi ^{[1
]}

Macdonald, Simon J. F. ^{[2
]}

Keeling, Steve ^{[2
]}

Moses, John E. ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

[2] GlaxoSmithKline Inc, Med Res Ctr, Stevenage, Herts, England

来源：

CHEMICAL COMMUNICATIONS | 2010年 / 46卷 / 08期

基金：

英国工程与自然科学研究理事会;

关键词：

ISOQUINOLINIUM N-ARYLIMIDES; COPPER-FREE CLICK; EFFICIENT SYNTHESIS; ORGANIC-SYNTHESIS; BOND FORMATION; DERIVATIVES; ARYNES; CHEMISTRY; BENZOTRIAZOLES; DIAZOMETHANE;

D O I：

10.1039/b922489k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient synthesis of a range of 1,2-benzisoxazoles using an improved 1,3-dipolar cycloaddition of nitrile oxides and benzyne is described. Key to the procedure is the in situ generation of the reactive nitrile oxide and benzyne reaction partners mediated by TBAF. Reactions are complete within 30 s, giving the target products in good to excellent yield.

引用

页码：1272 / 1274

页数：3

共 54 条

[1]

Bast K, 1998, EUR J ORG CHEM, V1998, P379

[2]

Bastos MM, 2001, J BRAZIL CHEM SOC, V12, P417

[3] The action of alkali on acylated ketoximes III Hydrogen bond formation in derivatives of the o-hydroxybenzophenone oximes [J].

Blatt, AH ;

Russell, LA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1936, 58 :1903-1908

[4] Copper-free 'click': 1,3-dipolar cycloaddition of azides and arynes [J].

Campbell-Verduyn, Lachlan ;

Elsinga, Philip H. ;

Mirfeizi, Leila ;

Dierckx, Rudi A. ;

Feringa, Ben L. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (19) :3461-3463

[5] 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

[6] CHLORINATION OF OXIMES .1. REACTION AND MECHANISM OF CHLORINATION OF OXIMES IN COMMERCIAL CHLOROFORM AND METHYLENE CHLORIDE [J].

CHIANG, YH .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (15) :2146-&

[7] FLUORIDE-ION AS A BASE IN ORGANIC-SYNTHESIS [J].

CLARK, JH .

CHEMICAL REVIEWS, 1980, 80 (05) :429-452

[8] 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

[9] Preparation of 3-(4-pyridinylamino)-1,2-benzisoxazoles via a nucleophilic aromatic substitution reaction [J].

Fink, DM ;

Kurys, BE .

TETRAHEDRON LETTERS, 1996, 37 (07) :995-998

[10]

Gabbert J F, 1997, Am J Ther, V4, P159, DOI 10.1097/00045391-199704000-00008

← 1 2 3 4 5 6 →