3340-79-2Relevant articles and documents
Solvent-driven C(sp3)-H thiocarbonylation of benzylamine derivatives under catalyst-free conditions
Zhou, Jingwei,Wang, Songping,Lu, Yaoming,Li, Lamei,Duan, Wentao,Wang, Qi,Wang, Hong,Wei, Wentao
supporting information, p. 767 - 773 (2021/02/09)
Due to the particularity of the thiocarbonyl group (C S bond), only limited C(sp3)-H thiocarbonylation methods, especially efficient and convenient methods, have been developed for the synthesis of thioamides. Inspired by the “solvent-specifici
Bronsted acid cocatalysts in photocatalytic radical addition of α-amino C-H bonds across michael acceptors
Ruiz Espelt, Laura,Wiensch, Eric M.,Yoon, Tehshik P.
, p. 4107 - 4114 (2013/06/05)
In marked contrast to the variety of strategies available for oxidation and nucleophilic functionalization of methylene groups adjacent to amines, relatively few approaches for modification of this position with electrophilic reaction partners have been reported. In the course of an investigation of the reactions of photogenerated α-amino radicals with electrophiles, we made the surprising observation that the efficiency of radical photoredox functionalization of N-aryl tetrahydroisoquinolines is dramatically increased in the presence of a Bronsted acid cocatalyst. Optimized conditions provide high yields and efficient conversion to radical addition products for a range of structurally modified tetrahydroisoquinolines and enones using convenient household light sources and commercially available Ru(bpy)3Cl 2 as a photocatalyst. Our investigations into the origins of this unexpected additive effect have demonstrated that the carbon-carbon bond-forming step is accelerated by TFA and is a rare example of Bronsted acid catalysis in radical addition reactions. Moreover, a significant conclusion arising from these studies is the finding that product formation is dominated by radical chain processes and not by photocatalyst turnover. Together, these findings have important implications for the future design and mechanistic evaluation of photocatalytic radical processses.
Synthesis of 2-aryl-3,4-dihydroisoquinolin-2-ium bromides and their in Vitro acaricidal activity against Psoroptes cuniculi
Ma, Yan-Ni,Yang, Xin-Juan,Pan, Le,Hou, Zhe,Geng, Hui-Ling,Song, Xiao-Ping,Zhou, Le,Miao, Fang
, p. 204 - 211 (2013/03/14)
By employing sanguinarine, a natural active quaternary isoquinoline alkaloid, as a model molecule, a series of structurally simple quaternary 2-aryl-3,4-dihydroisoquinolin-2-ium compounds were designed and synthesized and evaluated for in vitro acaricidal activity against P. cuniculi. A new approach towards the title compounds was developed with isochroman as starting material. The results showed that 22 of 24 tested compounds displayed the activity in varying degrees at 0.4 mg/mL. Fourteen compounds were significantly more effective than ivermectin, a standard acaricide, and 6-methoxy dihydrosanguinarine, a derivative of sanguinarine (p0.05). And their comprehensive relative activity was 1.4 to 16.5 times than that of ivermectin and 1.5 to 18.8 times than that of 6-methoxy dihydrosanguinarine. The structure-activity relationship indicated that the introduction of a substituent to N-benzene ring, especially halogen atom and trifluoromethyl group, led to great improvement of the activity. The position of fluorine atom, methyl group and hydroxyl group made very significant effects on the activity. It was concluded that 2-aryl-3,4-dihydroisoquinolin- 2-iums are very promising candidates for the development of new isoquinoline acaricidal agents.
2-(substituted phenyl)-3,4-dihydroisoquinolin-2-iums as novel antifungal lead compounds: Biological evaluation and structure-activity relationships
Hou, Zhe,Yang, Rui,Zhang, Cen,Zhu, Li-Fei,Miao, Fang,Yang, Xin-Juan,Zhou, Le
, p. 10413 - 10424 (2013/10/22)
The title compounds are a class of structurally simple analogues of quaternary benzo[c]phenanthridine alkaloids (QBAs). In order to develop novel QBA-like antifungal drugs, in this study, 24 of the title compounds with various substituents on the N-phenylring were evaluated for bioactivity against seven phytopathogenic fungi using the mycelial growth rate method and their SAR discussed. Almost all the compounds showed definite activities in vitro against each of the test fungi at 50 μg/mL and a broad antifungal spectrum. In most cases, the mono-halogenated compounds 2-12 exhibited excellentactivities superior to the QBAs sanguinarine and chelerythrine. Compound 8 possessed the strongest activities on each of the fungi with EC50 values of 8.88-19.88 μg/mL and a significant concentration-dependent relationship. The SAR is as follows: the N-phenyl group is a high sensitive structural moiety for the activity and the characteristics and position of substituents intensively influence the activity. Generally, electron-withdrawing substituents remarkably enhance the activity while electron-donating substituents cause a decrease of the activity. In most cases, ortha- and para-halogenated isomers were more active than the corresponding m-halogenated isomers. Thus, the title compounds emerged as promising lead compounds for the development of novel biomimetic antifungal agrochemicals. Compounds 8 and 2 should have great potential as new broad spectrum antifungal agents for plant protection.
