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Communication

One-Pot Synthesis of Push–Pull Butadienes from 1,3-Diethyl-2-thiobarbituric Acid and Propargylic Alcohols

Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Julián Clavería 8, E-33006 Oviedo, Spain
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Academic Editor: Hideto Miyabe
Molbank 2022, 2022(3), M1393; https://doi.org/10.3390/M1393
Received: 27 May 2022 / Revised: 20 June 2022 / Accepted: 21 June 2022 / Published: 23 June 2022
(This article belongs to the Section Organic Synthesis)
A new synthetic procedure for obtaining two previously reported donor-acceptor butadiene dyes, namely 5-(3,3-bis(4-methoxyphenyl)allylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione and 5-(3,3-bis(4-(dimethylamino)phenyl)allylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione, based on the InCl3-catalyzed coupling 1,3-diethyl-2-thiobarbituric acid with 1,1-bis(4-methoxyphenyl)prop-2-yn-1-ol and 1,1-bis(4-(dimethylamino)phenyl)prop-2-yn-1-ol, respectively, is presented. The reactions, which cleanly proceed in water under MW irradiation, involve the initial generation of the corresponding enals by Meyer-Schuster rearrangement of the alkynols and their subsequent Knoevenagel condensation with the 2-thiobarbituric acid derivative. By following the same approach, the novel butadiene 5-(3,3-bi([1,1′-biphenyl]-4-yl)allylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione, which was characterized by 1H and 13C{1H} NMR, IR, UV-Vis, elemental analysis and HRMS, was synthesized in 79% yield. View Full-Text
Keywords: push–pull molecules; butadienes; indium chloride; propargylic alcohols; Meyer–Schuster rearrangement; Knoevenagel condensation; barbituric acid; microwave-assisted reactions push–pull molecules; butadienes; indium chloride; propargylic alcohols; Meyer–Schuster rearrangement; Knoevenagel condensation; barbituric acid; microwave-assisted reactions
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MDPI and ACS Style

Francos, J.; Cadierno, V. One-Pot Synthesis of Push–Pull Butadienes from 1,3-Diethyl-2-thiobarbituric Acid and Propargylic Alcohols. Molbank 2022, 2022, M1393. https://doi.org/10.3390/M1393

AMA Style

Francos J, Cadierno V. One-Pot Synthesis of Push–Pull Butadienes from 1,3-Diethyl-2-thiobarbituric Acid and Propargylic Alcohols. Molbank. 2022; 2022(3):M1393. https://doi.org/10.3390/M1393

Chicago/Turabian Style

Francos, Javier, and Victorio Cadierno. 2022. "One-Pot Synthesis of Push–Pull Butadienes from 1,3-Diethyl-2-thiobarbituric Acid and Propargylic Alcohols" Molbank 2022, no. 3: M1393. https://doi.org/10.3390/M1393

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