Unexpected reaction of dimethyl acetylenedicarboxylate with in situ generated arylketenes catalyzed by 1-methylimidazole

被引:38
作者
Ding, HF [1 ]
Ma, C [1 ]
Yang, YW [1 ]
Wang, YG [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
关键词
D O I
10.1021/ol050492q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An unexpected 1-methylimidazole-catalyzed reaction of dimethyl acetylenedicarboxylate (DMAD) with in situ generated arylketenes leading to the synthesis of dimethyl 2-arylidenesuccinates under mild conditions is described. A plausible mechanism has been proposed.
引用
收藏
页码:2125 / 2127
页数:3
相关论文
共 39 条
[21]   REACTION OF KETENE ALKYL TRIMETHYLSILYL ACETALS WITH DIMETHYL ACETYLENEDICARBOXYLATE CATALYZED WITH ZIRCONIUM TETRACHLORIDE [J].
MITANI, M ;
SUDOH, T ;
KOYAMA, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (06) :1683-1687
[22]   Novel pyridine-catalyzed reaction of dimethyl acetylenedicarboxylate with aldehydes and N-tosylimines:: Efficient synthesis of 2-benzoylfumarates and 1-azadienes [J].
Nair, V ;
Sreekanth, AR ;
Abhilash, N ;
Biju, AT ;
Devi, BR ;
Menon, RS ;
Rath, NP ;
Srinivas, R .
SYNTHESIS-STUTTGART, 2003, (12) :1895-1902
[23]   Novel pyridine-catalyzed reaction of dimethyl acetylenedicarboxylate with aldehydes: Formal [2+2] cycloaddition leading to 2-oxo-3-benzylidinesuccinates [J].
Nair, V ;
Sreekanth, AR ;
Vinod, AU .
ORGANIC LETTERS, 2001, 3 (22) :3495-3497
[24]   Triphenylphosphine promoted addition of dimethyl acetylenedicarboxylate to 1,2-benzoquinones: facile synthesis of novel gamma-spirolactones [J].
Nair, V ;
Nair, JS ;
Vinod, AU ;
Rath, NP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (21) :3129-3130
[25]   Theoretical predictions of substituent effects on the thermal electrocyclic ring openings of cyclobutenones [J].
Niwayama, S ;
Kallel, EA ;
Sheu, CM ;
Houk, KN .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) :2517-2522
[26]   Synthesis of highly functionalized gamma-butyrolactones from activated carbonyl compounds and dimethyl acetylenedicarboxylate [J].
Nozaki, K ;
Sato, N ;
Ikeda, K ;
Takaya, H .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) :4516-4519
[27]   CHEMISTRY OF SPIROKETALS [J].
PERRON, F ;
ALBIZATI, KF .
CHEMICAL REVIEWS, 1989, 89 (07) :1617-1661
[28]   REACTION OF KETENEALKYLSILYLACETALS WITH ETHYL PROPIOLATE [J].
QUENDO, A ;
ROUSSEAU, G .
TETRAHEDRON LETTERS, 1988, 29 (49) :6443-6446
[29]   PREPARATION AND REACTIVITY OF THE ADDUCTS OF KETENE ALKYLSILYL ACETALS WITH ETHYL PROPIOLATE IN THE PRESENCE OF TITANIUM TETRACHLORIDE [J].
QUENDO, A ;
ALI, SM ;
ROUSSEAU, G .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (25) :6890-6895
[30]   SYNTHESIS OF (+/-)-FOMANNOSIN [J].
SEMMELHACK, MF ;
TOMODA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (09) :2427-2428