Regioselective Metal-Free One-Pot Synthesis of Functionalized 2‑Aminothiophene Derivatives

A facile metal-free synthesis of 2-aminothiophene derivatives by the reaction of 2-ynals with thioamides in alcohols has been developed. This transformation allows the assembly of 2-aminothienyl ether derivatives via a well-designed aldol condensation/regioselective intramolecular cyclization/conjug...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-05, Vol.80 (9), p.4611-4617
Main Authors: Luo, Xiaoyan, Ge, Li-Shi, An, Xing-Lan, Jin, Jing-Hai, Wang, Yu, Sun, Pei-Pei, Deng, Wei-Ping
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Molecular Structure
Stereoisomerism
Thioamides - chemistry
Thiophenes - chemical synthesis
Thiophenes - chemistry
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Summary:A facile metal-free synthesis of 2-aminothiophene derivatives by the reaction of 2-ynals with thioamides in alcohols has been developed. This transformation allows the assembly of 2-aminothienyl ether derivatives via a well-designed aldol condensation/regioselective intramolecular cyclization/conjugate addition cascade reaction and provides a straightforward synthetic protocol for constructing 2,3,5-trisubstituted 2-aminothiophenes.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b00488