36244-17-4Relevant articles and documents
Preparation method of 2-trifluoromethyl substituted quinazolinone compound and application of 2-trifluoromethyl substituted quinazolinone compound in synthesis of pharmaceutical molecules
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Paragraph 0033; 0034; 0035; 0036; 0037; 0038; 0039; 0040, (2021/07/01)
The invention discloses a preparation method of a 2-trifluoromethyl substituted quinazolinone compound. The preparation method comprises the following steps: adding a palladium catalyst, a ligand, a carbon monoxide substitute, an additive, trifluoroethylimido acyl chloride and amine into an organic solvent, reacting at 110 DEG C for 16-30 hours, and after the reaction is completed, carrying out post-treatment to obtain the 2-trifluoromethyl substituted quinazolinone compound. The preparation method has the advantages of simple operation, cheap and easily available initial raw materials, high reaction efficiency, good substrate compatibility, synthesis of trifluoromethyl quinazolinone compounds substituted by different groups through substrate design, convenient operation, and broadening of the practicality of the method. The method is also successfully applied to the high-yield synthesis of the drug molecule Rutaecarpine.
A detailed study of the intramolecular hydroamination of N-(ortho-alkynyl)aryl-N′-substituted trifluoroacetamidines and bromodifluoroacetamidines
Zhu, Jiangtao,Xie, Haibo,Chen, Zixian,Li, Shan,Wu, Yongming
, p. 516 - 523 (2012/01/15)
The intramolecular hydroamination of N-(ortho-alkynyl)aryl-N′- substituted trifluoroacetamidines and bromodifluoroacetamidines is studied in detail. When the substituents on the alkyne fragment are aryl and alkyl groups, 5-endo-dig cyclization occurs utilizing NaAuCl4·2H 2O as a catalyst, while 6-exo-dig cyclization proceeds in the presence of K2CO3 as a base. Interestingly, the indole derivatives are afforded with good regioselectivity via a 5-endo-dig pathway catalyzed by Cu(OAc)2 when ortho-ethynyl appears on the aryl substituent of the amidine. The electrophilic cyclization of the amidines also shows good regioselectivity under the I2/NaHCO3 system. At the end, a facile cascade synthesis of fluorinated quinazolones is described via hydroamination/ozonolysis from the corresponding amidine.
