Stereoselective and regioselective synthesis of $N$-substituted methyl 2-((azolyl)methyl)-3-arylacrylates from Baylis--Hillman acetates

Abstract

N -Substituted methyl 2-((azolyl)methyl)-3-arylacrylates were synthesized stereo-and regioselectively with one-pot reaction between Baylis-Hillman acetates and a suitable acylazole in the presence of K 2 CO 3 as a base catalyst.The targeted N -substituted azole acrylates were efficiently obtained in good yields (39%-89%).

N-Acylazole mediated stereoselective and regioselective synthesis ofN-substituted azole acrylonitriles

“…Only one of the possible geometric isomers was obtained with the method used here, we concluded that the developed reactions are also found to be stereoselective. When the preparation of N -substituted azole acrylonitriles is compared with the preparation of N -substituted azole acrylates [18], different stereoisomers have been obtained. While Z -isomers of N -substituted azole acrylonitriles in this work are obtained, E -isomers of N -substituted azole acrylates in our previously published work have been obtained.…”

“…They were illustrated as valuable precursors for the synthesis of heterocycles and many biologically active molecules [16,17]. We recently reported the synthesis of several N -substituted azole acrylates from the reaction between Baylis-Hillman adducts and N -acylazoles with quantitative yields in one-pot reaction [18]. N -Acylazoles are very important synthetic auxiliaries in organic synthesis as they are stable crystalline compounds and offer mild reaction conditions to prepare amides [19,20], esters, thioesters [21], ketones [22,23], and heterocycles [24][25][26].…”

Synthesis and Evaluation of Baylis-Hillman Reaction Derived Imidazole and Triazole Cinnamates as Antifungal Agents

“…The isomerization of BH acetates or bromides with imidazole or triazoles provides facile access to functionalized allyl imidazoles or allyl triazoles [ 25 – 29 ]. This protocol allows high flexibility and rapid access to structurally diverse functionalized allyl imidazoles and triazoles.…”