Abstract: For the first time, the multicomponent reaction of 2-aminothiophenes with α-ketoaldehydes and Meldrum's acid was investigated. 2-aminothiophene-3-carboxylic acids were utilized as easily available starting materials for generation of labile 2-aminothiophenes in the reaction mixture. We have shown that depending on the structure of employed 2-aminothiophenes and conditions of the process two types of final products can be obtained. As a rule, the presented multicomponent condensation leads to the formation of diverse 4-aroyl-4,7-dihydrothieno[2,3-b]pyridin-6(5H)-ones. At the same time, along with aforementioned products triethylammonium salts of 2,2-dimethyl-5-(5-aryl-6H-thieno[2,3-b]pyrrol-4-yl)-1,3-dioxane-4,6-diones can be prepared applying 2-aminothiophenes with carboxamide unit in position 5. Based on the performed investigation the general method for the synthesis of 4-aroyl-4,7-dihydrothieno[2,3-b]pyridin-6(5H)-ones was elaborated allowing to obtain 29 examples of compounds of this class with yields up to 69%. The advantages of the developed approach are simple experimental conditions, atom economy and facile isolation of target products without chromatographic purification. The structures of two synthesized thieno[2,3-b]pyridin-6(5H)-ones were unambiguously confirmed using X-ray analysis.

Cite: Lichitsky B.V. , Zholtovskaya A.A.
Study of the multicomponent reaction of 2-aminothiophenes with arylglyoxals and Meldrum's acid.
Tetrahedron. 2026. V.198. 135360 . DOI: 10.1016/j.tet.2026.135360 Scopus OpenAlex

Dates:

Submitted:	Mar 9, 2026
Published online:	Jun 3, 2026

Identifiers:

≡ Scopus:	2-s2.0-105040773871
≡ OpenAlex:	W7162799187

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