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.
Metal-Free Annulation of 2-Nitrobenzyl Alcohols and Tetrahydroisoquinolines toward the Divergent Synthesis of Quinazolinones and Quinazolinethiones
Le, Nhan T. H.,Ly, Duc,Nguyen, Khang X.,Nguyen, Thao T.,Nguyen, Tung T.,Nguyen, Vy P. T.,Pham, Phuc H.,Phan, Nam T. S.,Tran, Cam T. H.
, (2022/01/03)
A simple metal-free method for the synthesis of quinazolinones from commercially available 2-nitrobenzyl alcohols and tetrahydroisoquinolines is developed. The reaction conditions were tolerant of an array of functionalities such as halogen, tertiary amine, protected alcohol, and ester groups. Under nearly identical conditions, quinazolinethiones were obtained in the presence of elemental sulfur and suitable mediators.
Visible-Light-Mediated Synthesis of Rutaecarpine Alkaloids through C-N Cross-Coupling Reaction
Chen, Dong,Li, Shiqing,Wang, Jinhua,Gou, Tiantian,Zhang, Linfeng,Wang, Guixia,Kong, Xiangfei
, p. 987 - 992 (2021/04/21)
A visible-light-initiated cross-dehydrogenative-coupling amination is described, featuring metal- and photocatalyst-free, at room temperature, and using air as an oxidant. The reaction provides a facile approach for the synthesis of rutaecarpine and its derivatives. The substrates with electron-withdrawing groups give higher yields than those with electron-donating groups, but the substituent position has a negligible influence on the yield. Using binaphthyl-diyl hydrogen phosphate and dibenzyl phosphate as catalysts both deliver satisfying yields. This straightforward light-driven strategy might be applicable to the synthesis of quinazolinone derivatives.
