84-26-4Relevant articles and documents
Cytotoxic hybrids between the aromatic alkaloids bauerine C and rutaecarpine
Huber, Kilian,Bracher, Franz
, p. 1313 - 1316 (2007)
Two hybrids between the alkaloids bauerine C and rutaecarpine were prepared. Screening for cytotoxic activity revealed that introduction of two chlorine substituents to the quinazolinocarboline core of rutaecarpine strongly enhances cytotoxic activity, wh
Synthesis of 1-Thio-Substituted Isoquinoline Derivatives by Tandem Cyclization of Isothiocyanates
Wen, Li-Rong,Dou, Qian,Wang, Yuan-Chao,Zhang, Jin-Wei,Guo, Wei-Si,Li, Ming
, p. 1428 - 1436 (2017)
A copper-catalyzed tandem arylation-cyclization process to access 1-(arylthio)isoquinolines from isothiocyanates and diaryliodonium salts is described. It is the first general method to construct the potentially useful 1-(arylthio)isoquinoline derivatives. Moreover, 1-(methylthio)isoquinoline derivatives were also achieved successfully with MeOTf instead of diaryliodonium salts under metal-free conditions. Mechanistic studies reveal that these two processes proceed in different routes. This method has been successfully applied to the synthesis of quinazolinone alkaloid rutaecarpine.
Preparation method of 2-trifluoromethyl substituted quinazolinone compound and application of 2-trifluoromethyl substituted quinazolinone compound in synthesis of pharmaceutical molecules
-
, (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.
Copper-catalyzed synthesis of pyrido-fused quinazolinones from 2-aminoarylmethanols and isoquinolines or tetrahydroisoquinolines
Ly, Duc,Nguyen, Duyen K.,Nguyen, Khang X.,Nguyen, Khoa D.,Nguyen, Thao T.,Nguyen, Tung T.,Pham, Phuc H.,Phan, Nam T. S.
supporting information, p. 4726 - 4732 (2021/06/09)
Pyrido-fused quinazolinones were synthesizedviacopper-catalyzed cascade C(sp2)-H amination and annulation of 2-aminoarylmethanols with isoquinolines or pyridines. The transformation proceeded readily in the presence of a commercially available CuCl2catalyst with molecular oxygen as a green oxidant. Moreover, the dehydrogenative cross-coupling of 2-aminoarylmethanols with tetrahydroisoquinolines was explored, in which CuBr exhibited higher catalytic activity than CuCl2. Broad substrate scope with good tolerance of functionalities was observed under the optimized reaction conditions. The bioactive naturally occurring alkaloid rutaecarpine could be obtained by this strategy. The remarkable feature of this protocol is that complicated heterocyclic structures are readily achieved in a single synthetic step from easily accessible reactants and catalysts. This pathway to pyrido-fused quinazolinones would be complementary to existing protocols.