Sc(OTf)3-catalyzed or t-BuOK promoted tandem reaction of 2-(2-(alkynyl)benzylidene)malonate with indole

被引：53
作者：
Gao, Ke [1 ]
Wu, Jie [1 ,2 ]
机构：
[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
来源：
ORGANIC LETTERS | 2008年 / 10卷 / 11期
关键词：
D O I：
10.1021/ol800664z
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Tandem reaction of 2-(2-(alkynyl)benzylidene)malonate with indole was investigated. (Z)-1-Benzylidene-3-(1H-indol-1-yl)-1H-indene-2,2(3H)-dicarboxylate was generated in the presence of t-BuOK at room temperature; whereas 3-((1H-indol-3-yl)(2-(alkynyl)aryl)methyl)-1H-indole was obtained when Sc(OTf)(3) was utilized as catalyst at 50 degrees C.
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页码：2251 / 2254
页数：4
相关论文
共 21 条
[1]   Generation and cyclization of a benzyne-tethered alkyllithium: Preparation of 4-substituted indans [J].
Bailey, WF ;
Longstaff, SC .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (03) :432-433
[2]   Highly regioselective synthesis of indene derivatives including an allene functional group via Pd/C-Catalyzed cyclization reaction in air [J].
Bi, Hai-Peng ;
Liu, Xue-Yuan ;
Gou, Fa-Rong ;
Guo, Li-Na ;
Duan, Xin-Hua ;
Liang, Yong-Min .
ORGANIC LETTERS, 2007, 9 (18) :3527-3529
[3]   Highly regio- and stereoselective synthesis of indene derivatives via electrophilic cyclization [J].
Bi, Hai-Peng ;
Guo, Li-Na ;
Duan, Xin-Hua ;
Gou, Fa-Rong ;
Huang, Shu-Hao ;
Liu, Xue-Yuan ;
Liang, Yong-Min .
ORGANIC LETTERS, 2007, 9 (03) :397-400
[4]   Synthesis of (+)-CP-263,114 [J].
Chen, C ;
Layton, ME ;
Sheehan, SM ;
Shair, MD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (30) :7424-7425
[5]   Tandem [4+2]/[3+2] cycloadditions of nitroalkenes [J].
Denmark, SE ;
Thorarensen, A .
CHEMICAL REVIEWS, 1996, 96 (01) :137-165
[6]   Lewis acid- and organocatalyst-cocatalyzed multicomponent reactions of 2-alkynylbenzaldehydes, amines, and ketones [J].
Ding, Qiuping ;
Wu, Jie .
ORGANIC LETTERS, 2007, 9 (24) :4959-4962
[7]   Highly regioselective synthesis of 2,3-disubstituted indenes via a novel palladium-catalyzed cyclization reaction of propargylic carbonates with carbon nucleophiles [J].
Duan, Xin-Hua ;
Guo, Li-Na ;
Bi, Hai-Peng ;
Liu, Xue-Yuan ;
Liang, Yong-Min .
ORGANIC LETTERS, 2006, 8 (25) :5777-5780
[8]   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
[9]   CARBON-CARBON DOUBLE-BOND CLEAVAGE WITH A HARD LEWIS ACID AND ETHANETHIOL [J].
FUJI, K ;
KAWABATA, T ;
NODE, M ;
FUJITA, E .
TETRAHEDRON LETTERS, 1981, 22 (09) :875-878
[10]   Synthesis of functionalized 1,2-dihydroisoquinolines via multicomponent one-pot reaction of 2-alkynylbenzaldehyde, amine, zinc, and allylic bromide or benzyl bromide [J].
Gao, Ke ;
Wu, Jie .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (22) :8611-8613
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