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Reaction of 3-Amino-4,6-diarylthieno[2,3-b]pyridine-2-carboxamides with Ninhydrin

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Abstract

The reaction of N-substituted amides of 3-amino-4,6-diarylthieno[2,3-b]pyridine-2-carboxylic acids with ninhydrin in the presence of catalytic amounts of sulfuric acid gave 1′-spiro[indene-2,2′-pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine]-1,3,4′(3′H)-triones. Structure of a number of key compounds was studied using 2D NMR spectroscopy; the bioavailability parameters of the obtained compounds in silico were calculated. In a laboratory experiment, a moderate antidote effect was revealed with respect to the 2,4-D herbicide for one compound.

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Funding

This work was financially supported by the Russian Foundation for Basic Research (project no. 19-43-230007 р_а_), the Administration of the Krasnodar Region, the Ministry of Education and Science of the Russian Federation (topic no. 0795-2020-0031). Biological studies were performed as part of the governmental task of the Ministry of Science and Higher Education of the Russian Federation (no. 075-00376-19-00, and grant no. 0686-2019-0013).

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Authors and Affiliations

  1. Kuban State University, 350040, Krasnodar, Russia

    V. V. Dotsenko, V. S. Muraviev, D. Yu. Lukina & V. D. Strelkov

  2. North Caucasus University, 355009, Stavropol, Russia

    V. V. Dotsenko, N. A. Aksenov & I. V. Aksenova

  3. All-Russian Research Institute of Biological Plant Protection, 350039, Krasnodar, Russia

    V. S. Muraviev & L. V. Dyadyuchenko

  4. Kuban State Technological University, 350072, Krasnodar, Russia

    G. D. Krapivin

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  1. V. V. Dotsenko
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Dotsenko, V.V., Muraviev, V.S., Lukina, D.Y. et al. Reaction of 3-Amino-4,6-diarylthieno[2,3-b]pyridine-2-carboxamides with Ninhydrin. Russ J Gen Chem 90, 948–960 (2020). https://doi.org/10.1134/S1070363220060043

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