Intermolecular heterocyclization of alkynones with 2-mercaptoacetaldehyde under metal-free conditions: synthesis of 2,3-disubstituted thiophenes

[Display omitted] A concise and regioselective approach for the synthesis of 2,3-disubstituted thiophene derivatives has been developed. The synthetic strategy relies on the reaction of an in situ generated 2-mercaptoacetaldehyde with various alkynones. Furthermore, we calculated the energy gap betw...

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Bibliographic Details
Published in:Tetrahedron letters 2015-09, Vol.56 (40), p.5386-5389
Main Authors: Vatansever, Erol Can, Kılıç, Kübra, Özer, Merve Sinem, Koza, Gani, Menges, Nurettin, Balci, Metin
Format: Article
Language:English
Subjects:
2,3-Disubstituted thiophenes
2-Mercaptoacetaldehyde
Alkynes
Alkynones
Cyclization
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Summary:[Display omitted] A concise and regioselective approach for the synthesis of 2,3-disubstituted thiophene derivatives has been developed. The synthetic strategy relies on the reaction of an in situ generated 2-mercaptoacetaldehyde with various alkynones. Furthermore, we calculated the energy gap between the HOMO and the LUMO orbitals of all compounds and observed that the introduction of a strong electron-withdrawing group decreased the HOMO–LUMO energy gap.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.07.090