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A highly diastereoselective five-component synthesis of 1-(alkylimino)-5,5-dicyano-3a-aryloctahydro-3-oxacyclobuta[cd]pentalene-1a,2,5a,5b(2H,3aH)-tetracarboxylates

被引：20
作者：
Adib, Mehdi [1 ]
Sheikhi, Ehsan [1 ]
Haghshenas, Pouyan [1 ]
Rajai-Daryasarei, Saideh [1 ]
Bijanzadeh, Hamid Reza [2 ]
Zhu, Long-Guan [3 ]
机构：
[1] Univ Tehran, Univ Coll Sci, Sch Chem, Tehran, Iran
[2] Tarbiat Modares Univ, Dept Chem, Tehran, Iran
[3] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China
来源：
TETRAHEDRON LETTERS | 2014年 / 55卷 / 36期
关键词：
Isocyanides; Dialkyl acetylenedicarboxylates; Phenacyl bromides; Multicomponent reactions; 3-Oxacyclobuta[cd]pentalenes; Diastereoselective synthesis; MULTICOMPONENT REACTIONS; TERT-BUTYLISONITRILE; DIE DREIFACHBINDUNG; TERNARY COMPOUNDS; CONTROLLED ADDUCT; ISOCYANIDE; ACETYLENES; ADDITIONS; PHOSPHINES; VINYL;
D O I：
10.1016/j.tetlet.2014.07.007
中图分类号：
O62 [有机化学];
学科分类号：
070303 [有机化学];
摘要：
A novel one-pot, five-component synthesis of 1-(alkylimino)-5,5-dicyano-3a-aryloctahydro-3-oxacyclobuta[cd]pentalene-1a,2,5a,5b(2H,3aH)-tetracarboxylates is described. A mixture of phenacyl bromide, malononitrile, isocyanide, and two equivalents of a dialkyl acetylenedicarboxylate undergoes a novel 1:1:1:2 addition reaction at ambient temperature in absolute ethanol to produce diastereoselectively the title compounds in good yields. (C) 2014 Published by Elsevier Ltd.
引用
收藏
页码：4983 / 4986
页数：4
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