Access to Imidazo[1,2-a]pyridines via Annulation of α-Keto Vinyl Azides and 2-Aminopyridines
Praveen Reddy Adiyala, Geeta Sai Mani, Jagadeesh Babu Nanubolu, Kunta Chandra Shekar and Ram Awatar Maurya*
*Medicinal Chemistry and Pharmacology Division, CSIR-Indian
Institute of Chemical Technology (IICT), Hyderabad-500007, India, Email:
ram.cdri
gmail.com
P. R. Adiyala, G. S. Mani, J. B. Nanubolu, K. C. Shekar, R. A. Maurya, Org. Lett., 2015, 17, 4308-4311.
DOI: 10.1021/acs.orglett.5b02124
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Abstract
Efficient catalyst/metal-free annulations enable the synthesis of several imidazo[1,2-a]pyridines from readily available vinyl azides and 2-aminopyridines. In this remarkably high yielding and atom economical protocol, products can be isolated in highly pure form by simply evaporating the reaction solvent.
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General experimental procedure for the annulations of vinyl azides with 2-aminopyridines:
Vinyl azides (0.5 mmol), 2-aminopyridines (0.5 mmol), and dry THF (5 ml) were taken in a 10 mL round bottom flask and refluxed until the reaction was complete. Next, THF was evaporated under reduced pressure to yield the desired imidazo[1,2-a]pyridines. All the imidazo[1,2-a]pyridines were highly pure therefore no further purification was done.
Key Words
ID: J54-Y2015
