Application of Ynamides in the Synthesis of 2-(Tosylamido)- and 2,5-Bis(tosylamido)thiophenes
Application of Ynamides in the Synthesis of 2-(Tosylamido)- and 2,5-Bis(tosylamido)thiophenes
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DOI：
10.1021/acs.orglett.6b01101
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发表时间：
2016-06-03
期刊：
影响因子：
5.2
通讯作者：
Witulski, Bernhard
中科院分区：
文献类型：
--
作者：
Talbi, Imen;Alayrac, Carole;Witulski, Bernhard
本文报道了由不对称的1，3-丁二炔-1，4-二酰胺和1，3-丁二炔-1，4-二酰胺合成2-（对甲苯磺酰氨基）-和2，5-双（对甲苯磺酰氨基）-噻吩的一种分步经济的无金属催化剂的方法。该反应在Na 2S中心点9 H（2）O（2-3当量）存在下在温和的反应条件（50 ℃）下进行，并且通过在双酰亚胺中的极化碳碳三键来促进。这种新的方法噻吩的基础上的化学的双（对甲苯磺酰氨基）封端的三噻吩具有一串的N，S-杂原子嵌入在一个高度π共轭的分子框架的合成。
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.