Strategies for heterocyclic construction via novel multicomponent reactions based on isocyanides and nucleophilic carbenes

被引:854
作者
Nair, V [1 ]
Rajesh, C [1 ]
Vinod, AU [1 ]
Bindu, S [1 ]
Sreekanth, AR [1 ]
Mathen, JS [1 ]
Balagopal, L [1 ]
机构
[1] CSIR, Organ Chem Div, Trivandrum 695019, Kerala, India
关键词
D O I
10.1021/ar020258p
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This Account focuses mainly on our recent endeavors in the area of multicomponent reactions (MCRs) involving zwitterionic species generated by the addition of isocyanides and nucleophilic carbenes such as dimethoxycarbene and N-heterocyclic carbenes to activated alkynes. The strategy employed encompasses the interception of 1:1 zwitterionic species, generated in situ with a wide range of electrophiles. The new MCRs developed offer an efficient and convenient entry into several heterocycles of biological and synthetic importance.
引用
收藏
页码:899 / 907
页数:9
相关论文
共 59 条
[2]   A STABLE CRYSTALLINE CARBENE [J].
ARDUENGO, AJ ;
HARLOW, RL ;
KLINE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363
[3]   Highly diastereoselective cycloisomerization of acyclic trienones. The interrupted Nazarov reaction [J].
Bender, JA ;
Blize, AE ;
Browder, CC ;
Giese, S ;
West, FG .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2430-2431
[4]   Nazarov-initiated diastereoselective cascade polycyclization of aryltrienones [J].
Bender, JA ;
Arif, AM ;
West, FG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (32) :7443-7444
[5]  
Browder CC, 1999, SYNLETT, P1363
[6]   Highly efficient trapping of the Nazarov intermediate with substituted arenes [J].
Browder, CC ;
Marmsäter, FP ;
West, FG .
ORGANIC LETTERS, 2001, 3 (19) :3033-3035
[7]  
Denmark S. E., 1991, COMPREHENSIVE ORGANI, V5, P751
[8]  
Diels O, 1932, LIEBIGS ANN CHEM, V498, P16
[9]   ADDITIONS TO TERNARY COMPOUNDS .22. THERMODYNAMICALLY CONTROLLED ADDUCT FROM TERT-BUTYLISONITRILE AND ACETYLENECARBOXYLATE [J].
DILLINGER, HJ ;
FENGLER, G ;
SCHUMANN, D ;
WINTERFELDT, E .
TETRAHEDRON, 1974, 30 (15) :2561-2564
[10]   ADDITIONS TO TERNARY COMPOUNDS .21. KINETICALLY CONTROLLED ADDUCT FROM TERT-BUTYLISONITRILE AND ACETYLENEDICARBOXYLATE [J].
DILLINGER, HJ ;
FENGLER, G ;
SCHUMANN, D ;
WINTERFELDT, E .
TETRAHEDRON, 1974, 30 (15) :2553-2559