InCl3-catalyzed 5-exo-dig cyclization/1,6-conjugate addition of N-propargylamides with p-QMs to construct oxazole derivatives
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Guang-Ming Nan1, Xue Li1, Tian-Yu Yao2
1University and College Key Lab of Natural Product Chemistry and Application in Xinjiang, Yili Normal University, Yining 835000, China.
Abstract:
An InCl3-catalyzed atom-economic intramolecular 5-exo-dig cyclization/1,6-conjugate addition/aromatization of N-propargylamides with p-QMs to produce oxazoles tethering diarylmethane has been successfully developed. InCl3 not only served as Lewis acid to catalyze the cyclization of propargylic amides but also activated the carbonyl of p-QMs to achieve the 1,6-addition process in a one-pot manner. The reaction has attractive features, including mild reaction conditions, broad scope of substrates, good yields, and scalability.
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