Abstract
Readily available (chlorocarbonyl)phenyl ketene and a varied set of β-ketoamides were reacted in a one-step procedure to produce 2-pyrone derivatives. β-Ketoamide derivatives are versatile intermediates for the synthesis of heterocyclic compounds. For instance, 1-morpholino-3-phenyl-1,3-propanedione, 1-phenyl-3-piperidino-1,3-propanedione, 1-phenyl-3-pyrrolidino-1,3-propanedione, 1-piperidino-1,3-butanedione, 1-morpholino-2-phenyl ethanone were used in these reactions to produce 2-pyrone derivatives. In addition, the preparation of 4-hydroxy-3-phenylthiochromeno[4,3-b]pyran-2,5-dione derivatives and 4-hydroxy-7-methyl-3-phenyl pyrano[3,2-c]chromeno-2,5-dione were described. For the synthesis of these compounds 4-hydroxy-2H-thiochromen-2-ones and 4-hydroxy-8-methyl-2H-chromen-2-one were reacted with (chlorocarbonyl)phenyl ketene and the final products were isolated in good yields.
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The authors express appreciation to Shahid Bahonar University of Kerman, Faculty Research Committee for its support of this investigation.
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Dedicated with respect and admiration to Chemical Engineer Alireza Afzalipour the founder of Shahid Bahonar University of Kerman.
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Nejadshafiee, V., Abaszadeh, M., Saidi, K. et al. A one-pot reaction of (chlorocarbonyl) phenyl ketene with β-ketoamides and thiochromen-2-one. J IRAN CHEM SOC 10, 237–241 (2013). https://doi.org/10.1007/s13738-012-0146-8
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DOI: https://doi.org/10.1007/s13738-012-0146-8