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Tandem reaction of heterocyclic ketene aminals with diazoesters: Synthesis of pyrimidopyrrolidone derivatives
Institution:1. Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, PR China;2. Laboratory of Molecular Genetics of Aging and Tumor, Medical School, Kunming University of Science and Technology, Kunming, 650500, PR China;3. Biomedical Department, Yunnan Cancer Hospital, The Third Affiliated Hospital of Kunming Medical University, Kunming, 650118, PR China;1. Department of Chemistry, University of Calcutta, 92 APC Road, Kolkata 700009, India;2. Department of Materials Science, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700 032, India;1. Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China;2. Department of Medical Oncology, The Third Affiliated Hospital of Kunming Medical University, Yunnan Tumor Hospital, Kunming 650031, PR China;1. Istanbul Medipol University International School of Medicine, REMER (Regenerative and Restorative Medicine Research Center), Kavacık Campus, Kavacık/Beykoz-ISTANBUL, Turkey;2. Winston Salem State University, 311 W.B. Atkinson Bldg., 601 MLK, Jr., Winston Salem, NC 27110, United States;3. 101 N Chestnut St. APT 3, Winston Salem, NC 27101, United States;4. 1524 Trinity Garden Circle, Clemmons, NC 27012, United States;5. Chemistry Department, Wake Forest University, Salem Hall, Box 7486, Winston-Salem, NC 27109, United States
Abstract:A tandem reaction of heterocyclic ketene aminals (HKAs) with diazoesters in the presence of a Cu catalyst is demonstrated for the efficient synthesis of pyrimidopyrrolidone derivatives. The reaction shows a broad substrate scope and excellent functional group tolerance. Our method provides rapid access to diverse pyrimidopyrrolidones in moderate to excellent yields under mild reaction conditions.
Keywords:Tandem reaction  Heterocyclic ketene aminals  Diazoester  Pyrimidopyrrolidone
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