[4+1] Cycloaddition of Enaminothiones and Aldehyde N‐Tosylhydrazones Toward 3‐Aminothiophenes,Advanced Synthesis & Catalysis

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[4+1] Cycloaddition of Enaminothiones and Aldehyde N‐Tosylhydrazones Toward 3‐Aminothiophenes
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2018-10-08 , DOI: 10.1002/adsc.201801028
Zhuqing Liu _{1,

2} , Ping Wu _{1,

2} , Yuan He _{1,

2} , Ting Yang ₁ , Zhengkun Yu _{1,

3}

Affiliation

An efficient protocol toward trisubstituted 3‐aminothiophenes has been developed through a [4+1] cycloaddition of enaminothiones and aldehyde N‐tosylhydrazones under transition‐metal‐free conditions. 3‐Aminothiophene derivatives as well as their chiral analogs were obtained in good to excellent yields. Direct interaction of the enaminothiones with the diazo compounds of α‐carbonyl or ester group‐functionalized aldehydes also efficiently afforded the same type of 3‐aminothiophenes. The diversity of the synthetic methodology has been demonstrated by the broad substrate scopes and excellent chemoselectivity in cleavage of the C−S, C−O, and C−N bonds in enaminothiones.

中文翻译：

[4 + 1]烯胺硫酮和醛N-甲苯磺酰hydr向3-氨基噻吩的环加成反应

通过在无过渡金属条件下烯胺硫酮和醛N-甲苯磺酰s的[4 + 1]环加成反应，已开发出一种有效的三取代3-氨基噻吩方案。3-氨基噻吩衍生物及其手性类似物的收率良好。烯氨基硫酮与α-羰基或酯基官能化醛的重氮化合物的直接相互作用也有效地提供了相同类型的3-氨基噻吩。合成方法的多样性已通过广泛的底物范围和对烯胺硫酮的C-S，C-O和C-N键裂解的出色化学选择性证明。

更新日期：2018-10-08

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