4.7 Article

Access to 4,6-Diarylpicolinates via a Domino Reaction of Cyclic Sulfamidate Imines with Morita-Baylis-Hillman Acetates of Nitroolefins/Nitrodienes

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 10, Pages 4378-4385

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b00472

Keywords

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Funding

  1. DST [SB/S1/OC-19/2013]
  2. CSIR
  3. Government of India

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An interesting domino reaction of 5-membered cyclic sulfamidate imines with a variety of Morita-Baylis-Hillman acetates of nitroolefins/nitrodienes in the presence of DABCO as an organic base at 55 degrees C is reported for the first time. This new synthetic strategy provides a series of pharmacologically interesting 4,6-diarylpicolinates in high to excellent yields and allows several compatible functionalities on aryl rings. Moreover, the biologically interesting imidazo[1,2-a]pyridine (alpidem derivative) has been prepared in high chemical yield through a unique procedure.

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