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HPW-Catalyzed environmentally benign approach to imidazo 1,2-a pyridines #MMPMID38533469
Martinho LA; Andrade CKZ
Beilstein J Org Chem 2024[]; 20 (?): 628-637 PMID38533469show ga
The imidazo[1,2-a]pyridine moiety is present in drugs with several biological activities. The most direct way of obtaining this nucleus is the Groebke-Blackburn-Bienayme three-component reaction (GBB-3CR) between aminopyridines, aldehydes, and isocyanides under both Lewis and Bronsted acid catalysis. However, several catalysts for this reaction have major drawbacks such as being expensive, extremely dangerous, strong oxidizing, and even explosive. In this scenario, heteropolyacids emerge as greener and safer alternatives due to their very strong Bronsted acidity. In particular, phosphotungstic acid (HPW) is an economical and green attractive catalyst for being cheap, non-toxic, and is known for its chemical and thermal stability. Herein, we report a straightforward approach to the GBB-3CR using HPW as catalyst in ethanol under microwave (muw) heating. This convenient environmentally benign methodology is broad in scope, provides the heterobicyclic products in high yields (up to 99%), with a low catalyst loading (2 mol %) in only 30 minutes, and allows the successful use of aliphatic aldehydes, substrates not so frequently explored with most usual catalysts for this reaction. Furthermore, the aforementioned advantages make this methodology very attractive and superior to the existing ones.
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Beilstein+J+Org+Chem 2024 ; 20 (?): 628-637
