Synthesis of <scp>9</scp> <i>H</i> ‐Indeno[1,2‐ <i>b</i> ]Thieno[2,3‐ <i>e</i> ]Pyridin‐9‐One System Based on Multicomponent Reaction of 3‐Aminothiophenes With Aldehydes and 1,3‐Indandione

ABSTRACT For the first time, the multicomponent reaction of 3‐aminothiophenes with various aldehydes and 1,3‐indandione was studied. The unstable starting 3‐aminothiophenes were generated in situ from the corresponding sodium salts of 3‐aminothiophene‐2‐carboxylic acids. We have shown that the considered interaction allows us to construct the 9 H ‐indeno[1,2‐ b ]thieno[2,3‐ e ]pyridin‐9‐one system. A straightforward, one‐step approach to a wide range of target polycyclic products was developed based on the presented multicomponent condensation. Using this method, 21 examples of substituted 9 H ‐indeno[1,2‐ b ]thieno[2,3‐ e ]pyridin‐9‐ones were obtained with yields of up to 76%. The advantages of the designed synthetic route are atom economy, readily accessible starting materials, and a convenient procedure for the isolation of final compounds, avoiding chromatography. The structure of one of the prepared 9 H ‐indeno[1,2‐b]thieno[2,3‐ e ]pyridin‐9‐ones was unambiguously proved using x‐ray diffraction.

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Journal
Journal of Heterocyclic Chemistry
Published
2025-09-22
DOI
https://doi.org/10.1002/jhet.70107
Primary Topic
Multicomponent Synthesis of Heterocycles
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article
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article

Synthesis of 9 H ‐Indeno[1,2‐ b ]Thieno[2,3‐ e ]Pyridin‐9‐One System Based on Multicomponent Reaction of 3‐Aminothiophenes With Aldehydes and 1,3‐Indandione

T. A. Kudryavtseva, Boris V. Lichitsky, Ekaterina Kudryavtseva
Journal of Heterocyclic Chemistry
Multicomponent Synthesis of Heterocycles
article

Synthesis of 9 H ‐Indeno[1,2‐ b ]Thieno[2,3‐ e ]Pyridin‐9‐One System Based on Multicomponent Reaction of 3‐Aminothiophenes With Aldehydes and 1,3‐Indandione

T. A. Kudryavtseva, Boris V. Lichitsky, Ekaterina Kudryavtseva
article en

Abstract

ABSTRACT For the first time, the multicomponent reaction of 3‐aminothiophenes with various aldehydes and 1,3‐indandione was studied. The unstable starting 3‐aminothiophenes were generated in situ from the corresponding sodium salts of 3‐aminothiophene‐2‐carboxylic acids. We have shown that the considered interaction allows us to construct the 9 H ‐indeno[1,2‐ b ]thieno[2,3‐ e ]pyridin‐9‐one system. A straightforward, one‐step approach to a wide range of target polycyclic products was developed based on the presented multicomponent condensation. Using this method, 21 examples of substituted 9 H ‐indeno[1,2‐ b ]thieno[2,3‐ e ]pyridin‐9‐ones were obtained with yields of up to 76%. The advantages of the designed synthetic route are atom economy, readily accessible starting materials, and a convenient procedure for the isolation of final compounds, avoiding chromatography. The structure of one of the prepared 9 H ‐indeno[1,2‐b]thieno[2,3‐ e ]pyridin‐9‐ones was unambiguously proved using x‐ray diffraction.

Journal of Heterocyclic ChemistryVol. 62(12)
N.D. Zelinsky Institute of Organic Chemistry (RU)
Openalex Percentile: Top 80%
Multicomponent Synthesis of Heterocycles
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