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One-Pot Synthesis of Trifluoromethylated Quinazolin-4(3 H)-ones with Trifluoroacetic Acid as CF3 Source.

  • Almeida S Chemical Development , Idorsia Pharmaceuticals Ltd. , Hegenheimermattweg 91 , 4123 Allschwil , Switzerland.
  • Marti R HES-SO, University of Applied Sciences Western Switzerland , Haute Ecole d'Ingénierie et d'Architecture Fribourg, Institute of Chemical Technology , Boulevard de Pérolles 80 , CH-1700 Fribourg , Switzerland.
  • Vanoli E HES-SO, University of Applied Sciences Western Switzerland , Haute Ecole d'Ingénierie et d'Architecture Fribourg, Institute of Chemical Technology , Boulevard de Pérolles 80 , CH-1700 Fribourg , Switzerland.
  • Abele S Chemical Development , Idorsia Pharmaceuticals Ltd. , Hegenheimermattweg 91 , 4123 Allschwil , Switzerland.
  • Tortoioli S Chemical Development , Idorsia Pharmaceuticals Ltd. , Hegenheimermattweg 91 , 4123 Allschwil , Switzerland.
  • 2018-04-13
Published in:
  • The Journal of organic chemistry. - 2018
Catalysis
Chemistry Techniques, Synthetic
Methylation
Quinazolines
Trifluoroacetic Acid
English A novel and convenient one-pot sequential cascade method for the preparation of 2-trifluoromethylquinazolin-4(3 H)-ones is described. Trifluoroacetic acid (TFA) was employed as inexpensive and readily available CF3 source, which in the presence of T3P was condensed with a variety of anthranilic acids and amines to provide the products in up to 75% yield. The protocol was proved to be robust on 80 g scale, and the synthetic versatility of the prepared quinazolinon-4-ones was demonstrated by derivatization to further useful building blocks.
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  • English
Open access status
green
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https://sonar.ch/global/documents/276266
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