Application of Ynamides in the Synthesis of 2-(Tosylamido)- and 2,5-Bis(tosylamido)thiophenes

被引：27
作者：
Talbi, Imen [1 ,2 ,3 ]
Alayrac, Carole [1 ,2 ]
Lohier, Jean-Francois [1 ,2 ]
Touil, Soufiane [3 ]
Witulski, Bernhard [1 ,2 ]
机构：
[1] Normandie Univ, ENSICAEN, CNRS UMR 6507, Lab Chim Mol & Thioorgan, 6 Bvd Marechal Juin, F-14050 Caen, France
[2] UNICAEN, 6 Bvd Marechal Juin, F-14050 Caen, France
[3] Univ Carthage, Fac Sci Bizerte, Lab Heteroatom Organ Chem, Jarzouna 7021, Tunisia
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 11期
关键词：
BETA-AMYLOID PLAQUES; THIOPHENES; DERIVATIVES; CHROMOPHORES; HETEROCYCLES; ENHANCEMENT; 1,3-DIYNES; AMIDATION; AMINATION; SULFUR;
D O I：
10.1021/acs.orglett.6b01101
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A step-economic and metal-catalyst-free synthesis of 2-(tosylamido)- and 2,5-bis(tosylamido)-thiophenes from nonsymmetrical 1,3-butadiynamides and symmetrical 1,3-butadiyne-1,4-diamides is reported. The reaction proceeds in the presence of Na2S center dot 9H(2)O (2-3 equiv) under mild reaction conditions (50 degrees C) and is facilitated by polarized carbon carbon triple bonds in ynamides. This new approach to thiophenes based on the chemistry of ynamides was applied to the synthesis of a bis(tosylamido)-capped terthiophene having a string of N,S-heteroatoms embedded in a highly pi-conjugated molecular frame.
引用
收藏
页码：2656 / 2659
页数：4
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