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Microwave‐assisted synthesis and luminescent activity of imidazo[1,2‐ a ]pyridine derivatives
Author(s) -
Rodríguez Juan C.,
Maldonado Rony A.,
RamírezGarcía Gonzalo,
Díaz Cervantes Erik,
Cruz Fabiola N.
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3950
Subject(s) - chemistry , phenacyl bromide , pyridine , bromide , halogenation , luminescence , phenacyl , molecule , combinatorial chemistry , microwave irradiation , microwave , environmentally friendly , photochemistry , organic chemistry , catalysis , ecology , physics , optoelectronics , quantum mechanics , biology
In this work, a series of phenacyl bromide derivatives was synthesized and employed as key intermediate for the synthesis of substituted imidazo[1,2‐ a ]pyridines. First, phenacyl bromide molecules were obtained from the bromination reaction of acetophenones assisted by microwave irradiation, obtaining the products 4a‐v in a 15 minutes reaction with yields in the range of 50% to 99%. Subsequently, the conjugation of these molecules with 2‐aminopyridine conduced to the production of imidazo[1,2‐ a ]pyridine derivatives ( 7a‐v ) in a 60‐second reaction with yields of 24% to 99%. Improved yields were determined with respect to those obtained with more tedious methodologies like thermally and mechanically assisted routes. Intense luminescence emissions in the purple and blue regions of the electromagnetic spectra were observed under UV excitation according to the nature of the substituents. This environmentally friendly methodology is expected to constitute an important class of organic compounds for the development of biomarkers, photochemical sensors, and medicinal applications.