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Functionalization of the imidazo[1,2-a]pyridine ring in ?-phosphonoacrylates and ?-phosphonopropionates via microwave-assisted Mizoroki-Heck reaction.

ABSTRACT: A series of new phosphonocarboxylates containing an imidazo[1,2-a]pyridine ring has been synthesized via the microwave-assisted Mizoroki-Heck reaction. The efficient modification of the imidazo[1,2-a]pyridine ring has been achieved as late-stage functionalization, enabling and accelerating the generation of a library of compounds from a common precursor.

SUBMITTER: Kusy D

PROVIDER: S-EPMC6964661 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Functionalization of the imidazo[1,2-a]pyridine ring in α-phosphonoacrylates and α-phosphonopropionates via microwave-assisted Mizoroki-Heck reaction.

Kusy Damian D Wojciechowska Agata A Małolepsza Joanna J Błażewska Katarzyna M KM

Beilstein journal of organic chemistry 20200103

A series of new phosphonocarboxylates containing an imidazo[1,2-a]pyridine ring has been synthesized via the microwave-assisted Mizoroki-Heck reaction. The efficient modification of the imidazo[1,2-a]pyridine ring has been achieved as late-stage functionalization, enabling and accelerating the generation of a library of compounds from a common precursor. ...[more]

PMID: 31976012

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Project description:Background?-Bromination of the side chain of aromatic ketones using NBS in the presence of p-toluenesulfonic acid (p-TsOH) in acetonitrile is very common. However, regioselective bromination of bis and tris(?-bromoacetophenones) with NBS in the presence of p-TsOH in acetonitrile under microwave irradiation is quite novel. The bis- and tris(?-bromoacetophenones) are used in synthesis of bis and tris(heterocycles). bis(heterocycles) have received a great deal of attention, because many biologically active natural and synthetic products have molecular symmetry. The use of the pressurized microwave irradiation is very advantageous to many syntheses and provide a large rate enhancement.ResultsBis and tris(?-bromoacetophenones) were obtained as single monobrominated derivatives in a shorter time than the conventional conditions. The results clearly demonstrate the better reactivity and selectivity of NBS/p-TsOH/CH3CN as a brominating mixture under microwave conditions. The reaction of bis and tris(?-bromoacetophenone) with 2-aminopyridine and 2-aminopyrimidine proceeded smoothly in a mixture of anhydrous ethanol and DMF under reflux or using 300 W/105°C/ 20 min microwave irradiation conditions to afford the corresponding bis(imidazo[1,2-a]pyridine), bis(imidazo[1,2-a]pyrimidine) and tris(imidazo[1,2-a]pyridine) derivatives in moderate to excellent yields. The carbonyl analogue of the targeted bis(imidazopyridines) could be synthesized by the reaction of N,N-dimethyl-N'-(pyridin-2-yl)formimidamide with bis(?-bromoacetophenone) in refluxing ethanol. The structures of the newly synthesized compounds were confirmed by their spectral data as well as their elemental analyses.ConclusionIn conclusion, selective ?-bromination of bis- and tris(acetophenones) has been accomplished efficiently utilizing NBS/p-TsOH/CH3CN under microwave irradiation. In addition, a facile synthesis of novel series of bis- and tris(imidazopyridine) and bis(imidazopyrimidine) derivatives.

Dataset Information

Functionalization of the imidazo[1,2-a]pyridine ring in ?-phosphonoacrylates and ?-phosphonopropionates via microwave-assisted Mizoroki-Heck reaction.

Publications

Functionalization of the imidazo[1,2-<i>a</i>]pyridine ring in α-phosphonoacrylates and α-phosphonopropionates via microwave-assisted Mizoroki-Heck reaction.

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