Efficient Synthesis of Novel Biginelli and Hantzsch Products Sourced from Biorenewable Furfurals Using Gluconic Acid Aqueous Solution as the Green Organocatalyst.

Autor:	Anchan HN; Department of Chemistry, National Institute of Technology Karnataka (NITK), Surathkal, Mangalore,575025Karnataka ,India., Naik C P; Department of Chemistry, National Institute of Technology Karnataka (NITK), Surathkal, Mangalore,575025Karnataka ,India., Bhat NS; Department of Chemistry, National Institute of Technology Karnataka (NITK), Surathkal, Mangalore,575025Karnataka ,India., Kumari M; Department of Chemistry, National Institute of Technology Karnataka (NITK), Surathkal, Mangalore,575025Karnataka ,India., Dutta S; Department of Chemistry, National Institute of Technology Karnataka (NITK), Surathkal, Mangalore,575025Karnataka ,India.
Jazyk:	angličtina
Zdroj:	ACS omega [ACS Omega] 2023 Sep 06; Vol. 8 (37), pp. 34077-34083. Date of Electronic Publication: 2023 Sep 06 (Print Publication: 2023).
DOI:	10.1021/acsomega.3c05106
Abstrakt:	The Biginelli reaction provides 3,4-dihydropyrimidin-2(1 H )-ones (DHPMs), whereas the Hantzsch reaction leads to 1,4-dihydropyridines (DHPs) by the one-pot, multicomponent, and operationally simple transformations starting from readily available starting materials. DHPMs and DHPs are well-established heterocyclic moieties in the synthetic organic chemistry literature and have pronounced pharmacological activities. This work reports the synthesis of novel DHPMs and DHPs from carbohydrate-derived 5-substituted-2-furaldehydes by employing gluconic acid aqueous solution (GAAS) as an efficient, inexpensive, and eco-friendly catalyst. The use of urea (or thiourea) as the reagent led to DHPMs, whereas ammonium acetate produced DHPs, selectively, keeping the other two starting materials (i.e., furfurals and ethyl acetoacetate) and the reaction parameters unaltered. Using the general synthetic protocol under optimized reaction conditions (60 °C, 3-6 h, 25 mol % GAAS cat.), all the DHPM and DHP derivatives were obtained in good to excellent isolated yields. Competing Interests: The authors declare no competing financial interest. (© 2023 The Authors. Published by American Chemical Society.)
Databáze:	MEDLINE
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