Intramolecular Mannich reaction of 2-oxotryptamines with acetone yielding spiro[indole-3,3′-pyrrolidin]-2-ones

被引:4
作者
Incze, M [1 ]
Dörnyei, G [1 ]
Kajtár-Peredy, M [1 ]
Szántay, C [1 ]
机构
[1] Hungarian Acad Sci, Inst Chem, Chem Res Ctr, H-1025 Budapest 2, Hungary
关键词
intramolecular Mannich reaction; spirocyclic compounds; indoles; pyrrolidines; cyclizations; alkaloids;
D O I
10.1135/cccc19990408
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
2-Oxotryptamines undergo intramolecular Mannich-type cyclization with acetone to give 2',2'-dimethylspiro[indole-3,3'-pyrrolidin]-2-ones. In presence of an alkylating reagent, this reaction gives the corresponding 1'-substituted products.
引用
收藏
页码:408 / 416
页数:9
相关论文
共 10 条
[1]  
BAN Y, 1972, TETRAHEDRON LETT, P2113
[2]  
BAN Y, 1974, TETRAHEDRON LETT, P187
[3]  
DEMAINDREVILLE MD, 1981, B SOC CHIM FR II-CH, P179
[4]   HYDROXYTRYPTAMINES .4. SYNTHESIS AND REACTIONS OF 2-3'-OXINDOLYLETHYLAMINES [J].
HARLEYMASON, J ;
INGLEBY, RFJ .
JOURNAL OF THE CHEMICAL SOCIETY, 1958, (OCT) :3639-3642
[5]  
HENDRICKSON JB, 1963, J AM CHEM SOC, V84, P643
[6]   A SYNTHESIS OF SOME SPIRO [INDOLINE-3,3'-PYRROLIDINES] [J].
JANSEN, ABA ;
RICHARDS, CG .
TETRAHEDRON, 1965, 21 (06) :1327-&
[7]   Intramolecular acid-catalyzed aldolization of oxindolic methylketones [J].
Mirand, C ;
Papa, M ;
Cartier, D ;
Levy, J .
TETRAHEDRON LETTERS, 1997, 38 (13) :2263-2266
[8]  
OSHI T, 1968, TETRAHEDRON LETT, P491
[9]   Synthesis and biological evaluations of 3-substituted indolin-2-ones: A novel class of tyrosine kinase inhibitors that exhibit selectivity toward particular receptor tyrosine kinases [J].
Sun, L ;
Tran, N ;
Tang, F ;
App, H ;
Hirth, P ;
McMahon, G ;
Tang, C .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (14) :2588-2603
[10]  
SZABOPUSZTAY K, 1979, SYNTHESIS-STUTTGART, P276