Efficient Friedel-Crafts alkylation of indoles and pyrrole with enones and nitroalkene in water

被引:99
作者
Azizi, Najmedin
Arynasab, Fezzeh
Saidi, Mohammad R.
机构
[1] Chem & Chem Engn Res Ctr Iran, Organ Chem Lab, Tehran, Iran
[2] Sharif Univ Technol, Dept Chem, Tehran 11365, Iran
关键词
D O I
10.1039/b610263h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An operationally simple and entirely green protocol for heteropoly acid (10 mg) catalyst conjugate addition of indoles and pyrrole to unsaturated carbonyl compounds and nitroalkene in water at ambient temperature in good to excellent yields has been developed.
引用
收藏
页码:4275 / 4277
页数:3
相关论文
共 39 条
[11]   Direct coupling of indoles with carbonyl compounds: Short, enantioselective, gram-scale synthetic entry into the hapalindole and fischerindole alkaloid families [J].
Baran, PS ;
Richter, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7450-7451
[12]   The Michael addition of indoles to α,β-unsaturated ketones catalyzed by CeCl3•7H2O-NaI combination supported on silica gel [J].
Bartoli, G ;
Bartolacci, M ;
Bosco, M ;
Foglia, G ;
Giuliani, A ;
Marcantoni, E ;
Sambri, L ;
Torregiani, E .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4594-4597
[13]   The state of the art on Wells-Dawson heteropoly-compounds - A review of their properties and applications [J].
Briand, LE ;
Baronetti, GT ;
Thomas, HJ .
APPLIED CATALYSIS A-GENERAL, 2003, 256 (1-2) :37-50
[14]  
Chao J. L., 2005, CHEM REV, V105, P3095
[15]   Preparation of 5-substituted 1H-tetrazoles from nitriles in water [J].
Demko, ZP ;
Sharpless, KB .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) :7945-7950
[16]   Enantioselective indole Friedel-Crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes [J].
Evans, DA ;
Scheidt, KA ;
Fandrick, KR ;
Lam, HW ;
Wu, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10780-10781
[17]   The facile and efficient Michael addition of indoles and pyrrole to α, β-unsaturated electron-deficient compounds catalyzed by aluminium dodecyl sulfate trihydrate [Al(DS)3]3H2O in water [J].
Firouzabadi, H ;
Iranpoor, N ;
Nowrouzi, F .
CHEMICAL COMMUNICATIONS, 2005, (06) :789-791
[18]   Asymmetric Friedel-crafts alkylations of indoles with nitroalkenes catalyzed by Zn(II)-bisoxazoline complexes [J].
Jia, YX ;
Zhu, SF ;
Yang, Y ;
Zhou, QL .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) :75-80
[19]   Enantioselective synthesis of marine indole alkaloid hamacanthin B [J].
Jiang, B ;
Yang, CG ;
Wang, J .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (04) :1396-1398
[20]  
Kam T.-S., 1999, ALKAL CHEM, V14, P285