Interrupted nazarov cyclization on silica gel

被引:59
作者
Dhoro, F [1 ]
Tius, MA [1 ]
机构
[1] Univ Hawaii, Dept Chem, Honolulu, HI 96822 USA
关键词
D O I
10.1021/ja053393g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Exposure of a mixture of propargyl vinyl ketone and a nucleophilic primary or secondary amine to activated dry silica gel in the absence of solvent leads to a cascade of reactions that results in the formation of an aminocyclopentenone. The reaction with triethylamine leads to a cross-conjugated cyclopentadienone. Copyright © 2005 American Chemical Society.
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页码:12472 / 12473
页数:2
相关论文
共 20 条
[1]   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
[2]   Nazarov-initiated diastereoselective cascade polycyclization of aryltrienones [J].
Bender, JA ;
Arif, AM ;
West, FG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (32) :7443-7444
[3]   Efficient construction of benzohydrindenones from aryltrienones via domino Nazarov electrocyclization -: electrophilic aromatic substitution [J].
Browder, CC ;
Marmsäter, FP ;
West, FG .
CANADIAN JOURNAL OF CHEMISTRY, 2004, 82 (02) :375-385
[4]   Highly efficient trapping of the Nazarov intermediate with substituted arenes [J].
Browder, CC ;
Marmsäter, FP ;
West, FG .
ORGANIC LETTERS, 2001, 3 (19) :3033-3035
[5]   Isomerization-cyclization approach to the synthesis of 2-hydroxy-5-alkylidene-cyclopent-2-enones [J].
Forest, J ;
Bee, C ;
Cordaro, F ;
Tius, MA .
ORGANIC LETTERS, 2003, 5 (22) :4069-4072
[6]   The Nazarov cyclization in organic synthesis. Recent advances [J].
Frontier, AJ ;
Collison, C .
TETRAHEDRON, 2005, 61 (32) :7577-7606
[7]   Ionic hydrogenation of oxyallyl intermediates: the reductive Nazarov cyclization [J].
Giese, S ;
West, FG .
TETRAHEDRON, 2000, 56 (52) :10221-10228
[8]  
Giese S, 2000, ANGEW CHEM INT EDIT, V39, P1970, DOI 10.1002/1521-3773(20000602)39:11<1970::AID-ANIE1970>3.0.CO
[9]  
2-B
[10]  
Habermas K.L., 1994, ORG REACTIONS, V45, P1