Abstract:A rapid and efficient method for synthesis pyrimido[1,2‐a]benzimidazole derivatives from readily available starting materials is accomplished under microwave irradiation. This method has the advantages of short reaction time, operational simplicity, increased safety for small‐scale high‐speed synthesis, and minimal environment impact.
“…3 Analogs of this tricyclic system were synthesized by three component coupling under microwave irradiation and by using thiamine hydrochloride as a catalyst in aqueous conditions. [4][5][6][7] Attempts have been made in recent years to address the problem of discrimination of two regioisomeric products in the reactions of 2-aminobenzimidazoles, the origin which lies in the competing nucleophilicities of the 2-amino group and the ring nitrogen. 7 The variation on the active methylene component with ketoesters in ionic liquid medium has been reported and Sheibani et al demonstrated the multicomponent reaction of 2-aminobenzimidazole with ethyl-acyanocinnamoates in the presence of various base catalyst and the outcome of the product is differ from the present endeavor.…”
A telescoped sequence involves the reaction of cationic imidazolium attached 2-aminobenzimidazoles with in situ generated 1,1-dicyano-2-aryl ethylenes was explored for the regioselective synthesis of pyrimido[1,2-a]benzimidazoles. The perceived regioselectivity was presumed in terms of preferential Michael addition of 2-aminobenzimidazole followed by intramolecular annulation to the exclusive formation of 4-iminopyrimidines on an ionic liquid support. A plausible mechanistic pathway for their selective formation is discussed and fully supported by X-ray analysis. The present strategy reveals both the amine function and the ring nitrogen in substituted 2-aminobenzimidazoles are active sites for nucleophilic attack on a,b-unsaturated nitriles.
“…3 Analogs of this tricyclic system were synthesized by three component coupling under microwave irradiation and by using thiamine hydrochloride as a catalyst in aqueous conditions. [4][5][6][7] Attempts have been made in recent years to address the problem of discrimination of two regioisomeric products in the reactions of 2-aminobenzimidazoles, the origin which lies in the competing nucleophilicities of the 2-amino group and the ring nitrogen. 7 The variation on the active methylene component with ketoesters in ionic liquid medium has been reported and Sheibani et al demonstrated the multicomponent reaction of 2-aminobenzimidazole with ethyl-acyanocinnamoates in the presence of various base catalyst and the outcome of the product is differ from the present endeavor.…”
A telescoped sequence involves the reaction of cationic imidazolium attached 2-aminobenzimidazoles with in situ generated 1,1-dicyano-2-aryl ethylenes was explored for the regioselective synthesis of pyrimido[1,2-a]benzimidazoles. The perceived regioselectivity was presumed in terms of preferential Michael addition of 2-aminobenzimidazole followed by intramolecular annulation to the exclusive formation of 4-iminopyrimidines on an ionic liquid support. A plausible mechanistic pathway for their selective formation is discussed and fully supported by X-ray analysis. The present strategy reveals both the amine function and the ring nitrogen in substituted 2-aminobenzimidazoles are active sites for nucleophilic attack on a,b-unsaturated nitriles.
“…Shaaban 10 synthesised pyrimido [1,2a]benzimidazoles by the reaction of E-1-(1-methylbenzimidazol-2-yl)-3-(N,N-dimethylamino)prop-2-enone and 2-aminobenzimidazole in refluxing absolute ethanol catalysed by piperidine. Zhuang 11 developed a rapid and efficient method for the synthesis of pyrimido [1,2-a]benzimidazole derivatives under microwave irradiation. These approaches usually require forcing conditions, long reaction times, complex synthetic pathways and often, in organic solvents, the need for a catalyst.…”
A series of pyrimido[1,2-a]benzimidazole derivatives has been synthesised in high yields in the ionic liquid [bmim] + BF 4 − . The structures of the products were characterised by IR, 1 H NMR, and HRMS spectroscopy. The reaction work-up is simple and the ionic liquid is easily separated from the products for reuse.
Fused pyrimidine derivatives R 0515 A Rapid and Efficient Method for Synthesis of Pyrimido[1,2-a]benzimidazoleDerivatives under Microwave Irradiation. -(ZHUANG, Q.; LI, C.; TU*, S.; CAO, L.; ZHOU, D.; SHAO, Q.; GUO, C.; J.
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