Practical one-pot syntheses of ethyl 4-substituted-1H-pyrrole-3-carboxylates from aldehydes

被引:11
作者
Chang, Jay Hyok [1 ]
Shin, Hyunik [1 ]
机构
[1] LG Life Sci Ltd R&D, Chem Dev Div, Taejon 305380, South Korea
关键词
D O I
10.1021/op7002826
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Ethyl 4-substituted-1H-pyrrole-3-carboxylates were prepared in a one-pot manner starting from aromatic or aliphatic aldehydes via a Horner-Wadsworth-Emmons reaction and subsequent reaction with tosylmethylisocyanide (TosMIC) in the presence of sodium tert-amylate in toluene. Judicious selection of base and solvent led to the use of a single solvent, i.e., toluene, for reactions as well as for crystallization to render the one-pot process more practical and greener than the stepwise version.
引用
收藏
页码:291 / 293
页数:3
相关论文
共 10 条
[1]   DIFFERENTIAL REACTIVITY OF BETA-AMINO ENONES AND 3-DIMETHYLAMINOACRYLALDEHYDE TOWARDS ALPHA-AMINO DERIVATIVES [J].
ALBEROLA, A ;
ANDRES, JM ;
GONZALEZ, A ;
PEDROSA, R ;
VICENTE, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (10) :2681-2685
[2]   Efficient synthesis of 1-substituted-5-hydroxymethylimidazole derivatives: Clean oxidative cleavage of 2-mercapto group [J].
Chang, JH ;
Lee, KW ;
Nam, DH ;
Kim, WS ;
Shin, K .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2002, 6 (05) :674-676
[3]   A "bottom-up" approach to process development: Application of physicochemical properties of reaction products toward the development of direct-drop processes [J].
Chen, CK ;
Singh, AK .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2001, 5 (05) :508-513
[4]  
Katritzky AR, 1997, HETEROCYCLES, V44, P67
[5]   A novel class of highly potent, selective, and non-peptidic inhibitor of Ras farnesyltransferase (FTase) [J].
Lee, H ;
Lee, J ;
Lee, S ;
Shin, Y ;
Jung, WH ;
Kim, JH ;
Park, K ;
Kim, K ;
Cho, HS ;
Ro, S ;
Lee, S ;
Jeong, S ;
Choi, T ;
Chung, HH ;
Koh, JS .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (23) :3069-3072
[6]   Efficient synthesis of 3-pyrrolylquinolines via an 1,3-dipolar cycloaddition/oxidation sequence [J].
Menasra, H ;
Kedjadja, A ;
Debache, A ;
Rhouati, S ;
Belfaitah, A ;
Carboni, B .
SYNTHETIC COMMUNICATIONS, 2005, 35 (21) :2779-2788
[7]   An efficient method for the synthesis of 3-arylpyrroles [J].
Pavri, NP ;
Trudell, ML .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2649-2651
[8]  
SHIN H, 2002, Patent No. 0162727
[9]   Solid-phase synthesis of pyrroles from enaminones and nitroalkenes [J].
Trautwein, AW ;
Jung, G .
TETRAHEDRON LETTERS, 1998, 39 (45) :8263-8266
[10]  
VANLEUSEN AM, 1972, TETRAHEDRON LETT, P5337