A Facile One‐pot Synthesis of Highly Functionalized Isoxazolyl Imidazo[1, 2‐a] Pyridines Through CuI‐Promoted Cyclization. (29th May 2014)

• Record Type: Journal Article
• Authors: Rajanarendar, E.; Reddy, K. G.; Krishna, S. R.; Srinivas, M.
• Is Part Of: Journal of heterocyclic chemistry. Volume 52:Number 3(2015)
• Page Start: 660
• Page End: 668
• Publication Date: 2014-05-29
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.2146
• Languages: English
• ISSNs: 0022-152X

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>A copper iodide‐promoted <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">cyclization</named-content> for the synthesis of isoxazolyl imidazo[1, 2‐<italic>a</italic>] pyridines <bold>3a</bold>, <bold>3b</bold>, <bold>3c</bold>, <bold>3d</bold>, <bold>3e</bold>, <bold>3f</bold>, <bold>3g</bold>, <bold>3h</bold>, <bold>3i</bold>, <bold>3j</bold> in a <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">one‐pot procedure</named-content> has been investigated by interaction of 2‐aminopyridines <bold>1a</bold>, <bold>1b</bold>, <bold>1c</bold>, <bold>1d</bold>, <bold>1e</bold> with nitrostyrylisoxazoles <bold>2a</bold>, <bold>2b</bold>, <bold>2c</bold>, <bold>2d</bold>, <bold>2e</bold>, <bold>2f</bold> under aerial oxidation condition. Similarly, the <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">one‐pot reaction</named-content> of 2‐amino pyridines <bold>1a</bold>, <bold>1b</bold>, <bold>1c</bold>, <bold>1d</bold>, <bold>1e</bold> with 4‐bromonitrostyrylisoxazole <bold>2d</bold> in the presence of copper iodide under aerial oxidation condition, followed by reaction with phenyl acetylenes <italic>in situ</italic> afforded highly functionalized imidazo[1, 2‐<italic>a</italic>]pyridines <bold>10a</bold>, <bold>10b</bold>, <bold>10c</bold>, <bold>10d</bold>, <bold>10e</bold>, <bold>10f</bold>, <bold>10g</bold>, <bold>10h</bold>, <bold>10i</bold>, <bold>10j</bold> by the <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">Sonogashira coupling</named-content>.</p> </abstract>