Regioselective synthesis of (E)-3-[2-(arylmethylene)-1-(arylsulfonyl)hydrazino]-2-propenoates via the reaction of arylsulfonyl hydrazones and alkyl propiolates in the presence of triphenylphosphine

被引:7
作者
Hashemi, Seyed Abolghasem [1 ]
机构
[1] Islamic Azad Univ, Dept Chem, Bushehr Branch, Bushehr, Iran
关键词
Regioselective reaction; Arylsulfonyl hydrazone; Triphenylphosphine; Alkyl propiolate; HETERO-MICHAEL ADDITION; DIAZO-COMPOUNDS; H INSERTION; IN-SITU; CYCLOPROPANATION; ALCOHOLS; NITROGEN; OXYGEN;
D O I
10.1016/j.tetlet.2012.07.055
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A regioselective method for the synthesis of (E)-3-[2-(arylmethylene)-1-(arylsulfonyl)hydrazino]-2-propenoates is described. The reaction takes place between arylsulfonyl hydrazones and alkyl propiolates in the presence of triphenylphosphine as the catalyst. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5141 / 5143
页数:3
相关论文
共 28 条
[1]   Sulfur-ylide-mediated synthesis of functionalized and trisubstituted epoxides with high enantioselectivity; Application to the synthesis of CDP-840 [J].
Aggarwal, VK ;
Bae, I ;
Lee, HY ;
Richardson, J ;
Williams, DT .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (28) :3274-3278
[2]   Catalytic cyclopropanation of alkenes using diazo compounds generated in situ. A novel route to 2-arylcyclopropylamines [J].
Aggarwal, VK ;
de Vicente, J ;
Bonnert, RV .
ORGANIC LETTERS, 2001, 3 (17) :2785-2788
[3]  
Aggarwal VK, 2001, ANGEW CHEM INT EDIT, V40, P1433, DOI 10.1002/1521-3773(20010417)40:8<1433::AID-ANIE1433>3.0.CO
[4]  
2-E
[5]   DIASTEREOSELECTIVITY IN THE O-H INSERTION REACTIONS OF RHODIUM CARBENOIDS DERIVED FROM PHENYLDIAZOACETATES OF CHIRAL ALCOHOLS - PREPARATION OF ALPHA-HYDROXY AND ALPHA-ALKOXY ESTERS [J].
ALLER, E ;
BROWN, DS ;
COX, GG ;
MILLER, DJ ;
MOODY, CJ .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (14) :4449-4460
[6]   LOW-COORDINATE HYPERVALENT PHOSPHORUS [J].
ARDUENGO, AJ ;
STEWART, CA .
CHEMICAL REVIEWS, 1994, 94 (05) :1215-1237
[7]   Straightforward Synthesis of Ethers: Metal-Free Reductive Coupling of Tosylhydrazones with Alcohols or Phenols [J].
Barluenga, Jose ;
Tomas-Gamasa, Maria ;
Aznar, Fernando ;
Valdes, Carlos .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (29) :4993-4996
[8]  
Barluenga J, 2009, NAT CHEM, V1, P494, DOI [10.1038/NCHEM.328, 10.1038/nchem.328]
[9]  
Berdinskii E. I., 1990, ORG KHIM, V26, P336
[10]  
Cacch S., 1997, SYNTHESIS-STUTTGART, P30