An efficient entry to 1,2-benzisoxazoles via 1,3-dipolar cycloaddition of in situ generated nitrile oxides and benzyne

被引:31
作者
Spiteri, Christian [1 ,2 ]
Mason, Christopher [1 ]
Zhang, Fengzhi [1 ]
Ritson, Dougal J. [1 ]
Sharma, Pallavi [1 ,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
基金
英国工程与自然科学研究理事会;
关键词
BASE-CATALYZED REARRANGEMENT; BOND FORMATION; DERIVATIVES; CHEMISTRY; OXIMES; INHIBITORS; POTENT; BENZISOXAZOLES; NUCLEOPHILES; DIMERIZATION;
D O I
10.1039/b927235f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient protocol for the 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 reactants simultaneously.
引用
收藏
页码:2537 / 2542
页数:6
相关论文
共 49 条
[1]   Novel base catalysed rearrangement of sultone oximes to 1,2-benzisoxazole-3-methane sulfonate derivatives [J].
Arava, Veera Reddy ;
Siripalli, Udaya Bhaskara Rao ;
Nadkarni, Vaishali ;
Chinnapillai, Rajendiran .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2007, 3
[2]  
BALASUBRAHMANYAM SN, 1988, INDIAN J CHEM B, V27, P793
[3]  
Belen'kii LI, 2008, NITRILE OXIDES, NITRONES, AND NITRONATES IN ORGANIC SYNTHESIS: NOVEL STRATEGIES IN SYNTHESIS, 2ND EDITION, P1
[4]   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
[5]  
Borsche W, 1939, LIEBIGS ANN CHEM, V540, P83
[6]   NEW FUROXAN CHEMISTRY .2. CHEMISTRY OF ACYL NITRILE OXIDES GENERATED INSITU BY THERMOLYSIS OF DIACYLFUROXANS [J].
BRITTELLI, DR ;
BOSWELL, GA .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (02) :316-320
[8]   REDUCTION OF SUBSTITUTED DELTA-2-ISOXAZOLINES - SYNTHESIS OF BETA-HYDROXY ACID-DERIVATIVES [J].
CURRAN, DP ;
SCANGA, SA ;
FENK, CJ .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (19) :3474-3478
[9]   CuI-mediated cross-coupling of aryl halides with oximes:: A direct access to O-aryloximes [J].
De, Prithwiraj ;
Nonappa ;
Pandurangan, Komala ;
Maitra, Uday ;
Wailes, Steve .
ORGANIC LETTERS, 2007, 9 (15) :2767-2770
[10]   BEHAVIOR OF NITRILE OXIDES TOWARDS NUCLEOPHILES .2. SUBSTITUENT EFFECT ON RATE OF DIMERIZATION OF AROMATIC NITRILE OXIDES TO 3,6-DIARYL-1,4,2,5-DIOXADIAZINES [J].
DESARLO, F ;
GUARNA, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1976, (06) :626-628