One-pot synthesis of trifluoromethylated quinazolin-4(3H)-ones with trifluoroacetic acid as CF3 source

Almeida, Sofia (School of Engineering and Architecture (HEIA-FR), HES-SO // University of Applied Sciences Western Switzerland ; Chemical Development, Idorsia Pharmaceuticals Ltd., Hegenheimermattweg 91, 4123 Allschwil, Switzerland) ; Marti, Roger (School of Engineering and Architecture (HEIA-FR), HES-SO // University of Applied Sciences Western Switzerland) ; Vanoli, Ennio (School of Engineering and Architecture (HEIA-FR), HES-SO // University of Applied Sciences Western Switzerland) ; Abele, Stefan (Chemical Development, Idorsia Pharmaceuticals Ltd., Hegenheimermattweg 91, 4123 Allschwil, Switzerland) ; Tortoioli, Simone (Chemical Development, Idorsia Pharmaceuticals Ltd., Hegenheimermattweg 91, 4123 Allschwil, Switzerland)

A novel and convenient one-pot sequential cascade method for the preparation of 2-trifluoromethylquinazolin-4(3H)-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.


Keywords:
Article Type:
scientifique
Faculty:
Ingénierie et Architecture
School:
HEIA-FR
Institute:
ChemTech - Institut des technologies chimiques
Subject(s):
Ingénierie
Date:
2018
Pagination:
10 p.
Published in:
The Journal of Organic Chemistry (JOC)
Numeration (vol. no.):
2018, 83, 9, pp. 5104-5113
DOI:
ISSN:
0022-3263
External resources:
Appears in Collection:

Note: The status of this file is: public


 Record created 2018-08-14, last modified 2019-03-26

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