Using the Sonogashira Reaction for Preparing a New Fragment Library based on the 3-alkynylimidazo[1,2-a]pyridine Scaffold

Author(s): Caroline Castera-Ducros , Hussein El-Kashef , Melanie Piednoel , Vincent Remusat , Jean-Claude Teulade , Pierre Verhaeghe , Pascal Rathelot , Patrice Vanelle .

Journal Name: Letters in Organic Chemistry

Volume 13 , Issue 7 , 2016

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Abstract:

Background: The imidazo[1,2-a]pyridine ring has been widely studied by medicinal chemists and displays great pharmaceutical potential.

Methods: In a view to prepare a library of new molecules including an imidazo[1,2-a]pyridine scaffold, as original fragments for the conception of novel anti-protozoal compounds, the Sonogashira crosscoupling reaction between 3-halogenoimidazo [1,2-a]pyridines and phenylacetylene was studied.

Results: From 3-iodoimidazo[1,2-a]pyridine, chosen as an optimal substrate for conducting the reaction at room temperature in 2 hours, a variety of terminal alkynes was involved into the reaction, leading to a series of 16 new 3-phenyethynylimidazo [1,2-a]pyridines in satisfying to good yields (50-82%) and 4 additional derivatives in moderate yields (30-40%).

Conclusion: Such synthetic approach appears efficient for the rapid synthesis of imidazopyridine chemical libraries. The corresponding derivatives will next be evaluated for their anti-infective properties.

Keywords: 3-halogenoimidazo[1, 2-a]pyridines, Sonogashira cross-coupling reaction, 3-alkynylimidazoimidazo[1, 2-a]pyridine.

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Article Details

VOLUME: 13
ISSUE: 7
Year: 2016
Page: [519 - 525]
Pages: 7
DOI: 10.2174/1570178613666160919124456
Price: $58

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