1,1′-Carbonyldiimidazole mediates the synthesis of N-substituted imidazole derivatives from Morita–Baylis–Hillman adducts

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

“…The overall yields seemed to be satisfactory and the double bond configurations of these compounds were assigned on the basis of 1 H NMR spectra and by comparing data available in the literature. 13,14,28 According to the literature, while the chemical shift value of the olefinic proton in the E-isomer is observed obviously downfield of the aromatic ring proton, the corresponding olefinic proton of the Z-isomer appears upfield. 28,29 When we went through the 1 H NMR spectra, we observed a chemical shift of a proton as a singlet appeared obviously downfield of the aromatic ring protons around 7.97-8.77 ppm for almost all compounds synthesized.…”

“…They were used as an intermediate to prepare poly-fused heterocycles 12 and as a substrate to synthesize ionic liquids. 13 A few methods have been developed for their preparation. In these literature methods, N -substituted azole acrylates were either prepared from an intermediate that was obtained through bromination or acetylation of Baylis-Hillman adducts in two steps 14,15 or they were directly prepared from Baylis-Hillman adducts in a single step using carbonyldiimidazole (CDI) 13 (Figure 2).…”

“…13 A few methods have been developed for their preparation. In these literature methods, N -substituted azole acrylates were either prepared from an intermediate that was obtained through bromination or acetylation of Baylis-Hillman adducts in two steps 14,15 or they were directly prepared from Baylis-Hillman adducts in a single step using carbonyldiimidazole (CDI) 13 (Figure 2). Although it is possible to access a wide range of azole derivatives using these methods, they still have some drawbacks, such as the use of highly reactive and toxic reagents to prepare starting compounds 17 or the need for previous activation of the OH group in Baylis-Hillman adducts.…”

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

“…The CN stretches in the IR spectra of 10 are similar to those observed for 9 and 9'. After all the compounds were synthesized and characterized, it was thought that only one isomer was formed among the possible geometric isomers E/Z that are said to have occurred for similar compounds in the literature [29][30][31][32]. According to the spectral data reported in the literature, while chemical shift values of the vinylic protons in the E -isomers appear obviously downfield of the aromatic protons, the corresponding values for the vinylic protons of the Z -isomers are generally observed upfield or overlapped with aromatic ring protons.…”

Development of Imidazole-Reactive Molecules Leading to a New Aggregation-Induced Emission Fluorophore Based on the Cinnamic Scaffold

“…Morita–Baylis–Hillman adducts (MBHAs) have been proposed to represent interesting reagents capable of alkylating imidazole by means of a concerted addition–elimination process. 21 Thus, owing to their high reactivity to imidazole in the presence of water, 22 MBHA derivatives could find applications as reagents for imidazole modification. For example, a successful alkylation of N -acetylhexahistidine with MBHA derivatives was performed by means of the aid of transition-metal cations interacting with a nitrilotriacetate ligand linked to an MBHA leaving group.…”