Michael addition of indoles to β-nitrostyrenes catalyzed by HY zeolite under solvent-free conditions

被引:30
作者
Jeganathan, Mariappan [1 ]
Kanagaraj, Kuppusamy [1 ]
Dhakshinamoorthy, Amarajothi [1 ,2 ]
Pitchumani, Kasi [1 ,2 ]
机构
[1] Madurai Kamaraj Univ, Sch Chem, Madurai 625021, Tamil Nadu, India
[2] Madurai Kamaraj Univ, Sch Chem, Ctr Green Chem Proc, Madurai 625021, Tamil Nadu, India
关键词
Michael addition; HY zeolite; Indole; beta-Nitrostyrenes; C-C bond formation; FRIEDEL-CRAFTS ALKYLATION; ELECTRON-DEFICIENT OLEFINS; ONE-POT SYNTHESIS; CONJUGATE ADDITION; HIGHLY EFFICIENT; LEWIS-ACIDS; NITROALKENES; NITROOLEFINS; DERIVATIVES; PYRROLE;
D O I
10.1016/j.tetlet.2014.01.112
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Michael addition of indoles to beta-nitrostyrenes is reported using HY zeolite as catalyst under mild reaction conditions. This methodology allows the synthesis of various indole derivatives in good to high yields at 50 C under solvent-free conditions. The short reaction time and achieving high yield of the desired products are the main advantages of the present work. The catalyst can be easily recovered and reused for six successive runs without considerable changes in yields. This Michael addition catalyzed by HY zeolite is operationally simple and can be considered as a greener protocol as it avoids the use of corrosive acids and toxic reagents. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2061 / 2064
页数:4
相关论文
共 49 条
[1]   Conjugate addition of indoles and thiols with electron-deficient olefins catalyzed by Bi(OTf)3 [J].
Alam, MM ;
Varala, R ;
Adapa, SR .
TETRAHEDRON LETTERS, 2003, 44 (27) :5115-5119
[2]  
[Anonymous], RODDS CHEM CARBON CO
[3]   Catalysis by zeolite leading to the construction of thiazole ring: an improved synthesis of 4-alkynyl substituted thiazoles [J].
Arunkumar, K. ;
Reddy, D. Naresh Kumar ;
Chandrasekhar, K. B. ;
Kumar, P. Rajender ;
Kumar, K. Shiva ;
Pal, Manojit .
TETRAHEDRON LETTERS, 2012, 53 (30) :3885-3889
[4]   Efficient Friedel-Crafts alkylation of indoles and pyrrole with enones and nitroalkene in water [J].
Azizi, Najmedin ;
Arynasab, Fezzeh ;
Saidi, Mohammad R. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (23) :4275-4277
[5]   H-Y zeolites induced heterocyclization:: Highly efficient synthesis of substituted-quinazolin-4(3H)ones under microwave irradiation [J].
Bakavoli, M. ;
Sabzevari, O. ;
Rahimizadeh, M. .
CHINESE CHEMICAL LETTERS, 2007, 18 (05) :533-535
[6]   One-pot synthesis of tetrasubstituted imidazoles catalyzed by zeolite HY and silica gel under microwave irradiation [J].
Balalaie, S ;
Arabanian, A .
GREEN CHEMISTRY, 2000, 2 (06) :274-276
[7]   Conjugate addition of indoles to nitroalkenes promoted by basic alumina in solventless conditions [J].
Ballini, R ;
Clemente, RR ;
Palmieri, A ;
Petrini, M .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (1-2) :191-196
[8]   A practical indium tribromide catalysed addition of indoles to nitroalkenes in aqueous media [J].
Bandini, M ;
Melchiorre, P ;
Melloni, A ;
Umani-ronchi, A .
SYNTHESIS-STUTTGART, 2002, (08) :1110-1114
[9]   Efficient preparation of 2-indolyl-1-nitroalkane derivatives employing nitroalkenes as versatile Michael acceptors:: New practical linear approach to alkyl 9H-β-Carboline-4-carboxylate [J].
Bartoli, G ;
Bosco, M ;
Giuli, S ;
Giuliani, A ;
Lucarelli, L ;
Marcantoni, E ;
Sambri, L ;
Torregiani, E .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (05) :1941-1944
[10]   Zeo-click synthesis: CuI-zeolite-catalyzed one-pot two-step synthesis of triazoles from halides and related compounds [J].
Beneteau, Valerie ;
Olmos, Andrea ;
Boningari, Thirupathi ;
Sommer, Jean ;
Pale, Patrick .
TETRAHEDRON LETTERS, 2010, 51 (28) :3673-3677