TY - JOUR
T1 - Use of imidazo[1,2-a]pyridine as a carbonyl surrogate in a mannich-like, catalyst free, one-pot reaction
AU - Naresh, Gunaganti
AU - Lakkaniga, Naga Rajiv
AU - Kharbanda, Anupreet
AU - Yan, Wei
AU - Frett, Brendan
AU - Li, Hong Yu
N1 - Funding Information:
This work was supported by an Institutional Development Award (IDeA) from the National Institute of General Medical Sciences of the National Institutes of Health under grant number “P20 GM109005”. H. L. was supported by the grants NIH 1R01CA194094-010 and 1R01CA197178-01A1 and UAMS start-up funding. B. F. was supported by the UAMS Seeds of Science Grant, the UAMS COP Seed Grant, and a grant from the American Thyroid Association (ATA/Thyca).
Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2019/1/31
Y1 - 2019/1/31
N2 - Derivatization of imidazo[1,2-a]pyridine scaffolds have gained considerable attention due to the biological significance of therapeutics based on the imidazopyridine core. By utilizing a catalyst-free, “Mannich type” reaction, we developed a simple and efficient protocol to aminomethylate the C-3 position of imidazo[1,2-a]pyridine through a multicomponent, de-carboxylation reaction involving imidazo[1,2-a]pyridine, a secondary amine, and glyoxylic acid. The developed protocol re-quires mild reaction conditions and furnishes diverse imid-azo[1,2-a]pyridine analogues from commercially available starting materials. Additionally, the current protocol improves prior methods, which were limited by the amine substrate scope. Taken together, this current methodology permits rapid diversification of imidazo[1,2-a]pyridines to enhance combinatorial efficiency in the drug discovery processes.
AB - Derivatization of imidazo[1,2-a]pyridine scaffolds have gained considerable attention due to the biological significance of therapeutics based on the imidazopyridine core. By utilizing a catalyst-free, “Mannich type” reaction, we developed a simple and efficient protocol to aminomethylate the C-3 position of imidazo[1,2-a]pyridine through a multicomponent, de-carboxylation reaction involving imidazo[1,2-a]pyridine, a secondary amine, and glyoxylic acid. The developed protocol re-quires mild reaction conditions and furnishes diverse imid-azo[1,2-a]pyridine analogues from commercially available starting materials. Additionally, the current protocol improves prior methods, which were limited by the amine substrate scope. Taken together, this current methodology permits rapid diversification of imidazo[1,2-a]pyridines to enhance combinatorial efficiency in the drug discovery processes.
KW - Aminomethylation
KW - Catalyst-free reaction
KW - Heterocycles
KW - Mannich bases
KW - Multicomponent reactions
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U2 - 10.1002/ejoc.201801430
DO - 10.1002/ejoc.201801430
M3 - Article
AN - SCOPUS:85059676152
SN - 1434-193X
VL - 2019
SP - 770
EP - 777
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 4
ER -