Convenient indole synthesis from 2-iodoanilines and terminal alkynes by the sequential Sonogashira reaction and the cyclization reaction promoted by tetrabutylammonium fluoride (TBAF)

被引:37
作者
Suzuki, N [1 ]
Yasaki, S [1 ]
Yasuhara, A [1 ]
Sakamoto, T [1 ]
机构
[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan
关键词
indole; sequential cyclization; palladium-catalyzed reaction; 2-ethynylaniline; tetrabutylammnonium fluoride; terminal alkyne;
D O I
10.1248/cpb.51.1170
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The sequential Sonogashira reaction and the cyclization reaction of various 2-iodoanilines and terminal alkynes in the presence of a palladium catalyst and tetrabutylammonium fluoride (TBAF) gave the corresponding 2-substituted indoles in good yields.
引用
收藏
页码:1170 / 1173
页数:4
相关论文
共 20 条
[1]   Catalytic coupling of terminal acetylenes with iodoarenes and diaryliodonium salts in water [J].
Bumagin, NA ;
Sukhomlinova, LI ;
Luzikova, EV ;
Tolstaya, TP ;
Beletskaya, IP .
TETRAHEDRON LETTERS, 1996, 37 (06) :897-900
[2]   Recent developments in indole ring synthesis-methodology and applications [J].
Gribble, GW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (07) :1045-1075
[3]  
GRIBBLE GW, 1996, COMPREHENSIVE HETERO, V2, P207, DOI DOI 10.1016/B978-008096518-5.00043-5
[4]   Palladium-catalyzed cross-coupling of silanols, silanediols, and silanetriols promoted by silver(I) oxide [J].
Hirabayashi, E ;
Mori, A ;
Kawashima, J ;
Suguro, M ;
Nishihara, Y ;
Hiyama, T .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (17) :5342-5349
[5]   Pd(PhCN)2Cl2/P(t-Bu)3:: A versatile catalyst for sonogashira reactions of aryl bromides at room temperature [J].
Hundertmark, T ;
Littke, AF ;
Buchwald, SL ;
Fu, GC .
ORGANIC LETTERS, 2000, 2 (12) :1729-1731
[6]   Rapid microwave-enhanced, solventless Sonogashira coupling reaction on alumina [J].
Kabalka, GW ;
Wang, L ;
Namboodiri, V ;
Pagni, RM .
TETRAHEDRON LETTERS, 2000, 41 (27) :5151-5154
[7]  
Mori A, 2001, SYNLETT, P649
[8]  
Nakamura K, 1999, SYNLETT, P549
[9]  
SAKAMOTO T, 1988, CHEM PHARM BULL, V36, P1305
[10]   A NEW SYNTHESIS OF THE NATURALLY-OCCURRING FREE-RADICAL SCAVENGER CARAZOSTATIN [J].
SHIN, K ;
OGASAWARA, K .
CHEMISTRY LETTERS, 1995, (04) :289-290