Efficient Synthesis of Novel Biginelli and Hantzsch Products Sourced from Biorenewable Furfurals Using Gluconic Acid Aqueous Solution as the Green Organocatalyst.
ACS Omega
; 8(37): 34077-34083, 2023 Sep 19.
Article
en En
| MEDLINE
| ID: mdl-37744814
The Biginelli reaction provides 3,4-dihydropyrimidin-2(1H)-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.
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1
Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
ACS Omega
Año:
2023
Tipo del documento:
Article
País de afiliación:
India
Pais de publicación:
Estados Unidos