nBu3P-Catalyzed Desulfonylative [3+2] Cycloadditions of Allylic Carbonates with Arylazosulfones to Pyrazole Derivatives

被引：67

作者：

Zhang, Qi ^{[1
]}

Meng, Ling-Guo ^{[1
]}

Wang, Kuai ^{[1
]}

Wang, Lei ^{[1
,2
]}

机构：

[1] Huaibei Normal Univ, Dept Chem, Huaibei 235000, Anhui, Peoples R China

[2] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 04期

基金：

美国国家科学基金会;

关键词：

CATALYZED 4+2 ANNULATION; GAMMA-SUBSTITUENT ALLENOATES; DOMINO REACTION; PHOSPHINE CATALYSIS; SELECTIVE SYNTHESIS; HILLMAN CARBONATES; FACILE SYNTHESIS; SEQUENTIAL 2+3; N-TOSYLIMINES; CONSTRUCTION;

D O I：

10.1021/ol503735c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly efficient (Bu3P)-Bu-n-catalyzed desulfonylative [3 + 2] cycloadditions of allylic carbonates with arylazosulfones were developed for the synthesis of pyrazole derivatives. The reactions proceed smoothly under mild conditions to generate corresponding annulation products in good to excellent yields.

引用

页码：872 / 875

页数：4

共 56 条

[1] Natural Product Biosynthesis Inspired Concise and Stereoselective Synthesis of Benzopyrones and Related Scaffolds [J].

Baskar, Baburaj ;

Dakas, Pierre-Yves ;

Kumar, Kamal .

ORGANIC LETTERS, 2011, 13 (08) :1988-1991

[2]

Cao L., 2011, CHEM COMMUN, V47, P1045

[3] Highly Regio- and Diastereoselective Construction of Spirocyclopenteneoxindoles through Phosphine-Catalyzed [3+2] Annulation of Morita-Baylis-Hillman Carbonates with Isatylidene Malononitriles [J].

Deng, Hong-Ping ;

Wei, Yin ;

Shi, Min .

ORGANIC LETTERS, 2011, 13 (13) :3348-3351

[4] Lewis base catalysis in organic synthesis [J].

Denmark, Scott E. ;

Beutner, Gregory L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (09) :1560-1638

[5] A phosphine-catalyzed [3+6] annulation reaction of modified allylic compounds and tropone [J].

Du, YH ;

Feng, JQ ;

Lu, XY .

ORGANIC LETTERS, 2005, 7 (10) :1987-1989

[6] Highly regioselective construction of spirocycles via phosphine-catalyzed [3+2]-cycloaddition [J].

Du, YS ;

Lu, XY ;

Yu, YH .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :8901-8905

[7] ARYL ARYLAZO SULFONE CHEMISTRY .1. SYNTHESIS OF ARENES AND IODOARENES [J].

EVERS, MJ ;

CHRISTIAENS, LE ;

GUILLAUME, MR ;

RENSON, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (10) :1779-1780

[8] ARYL ARYLAZO SULFONES CHEMISTRY .2. REACTIVITY TOWARD ALKALINE ALKANE-SELENOLATE AND ARENESELENOLATE AND ALKANETELLUROLATE AND ARENETELLUROLATE ANIONS [J].

EVERS, MJ ;

CHRISTIAENS, LE ;

RENSON, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (26) :5196-5198

[9] Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs [J].

Fan, Yi Chiao ;

Kwon, Ohyun .

CHEMICAL COMMUNICATIONS, 2013, 49 (99) :11588-11619

[10] Cooperative, highly enantioselective phosphinothiourea catalysis of imine-allene [3+2] cycloadditions [J].

Fang, Yuan-Qing ;

Jacobsen, Eric N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (17) :5660-+

← 1 2 3 4 5 6 →