55662-90-3Relevant academic research and scientific papers
No photocatalyst required-versatile, visible light mediated transformations with polyhalomethanes
Franz, Johannes F.,Kraus, Wolfgang B.,Zeitler, Kirsten
supporting information, p. 8280 - 8283 (2015/05/13)
A visible light mediated, but photocatalyst-free method for the oxidative α-CH functionalization of tertiary amines with a broad scope of carbon- and heteroatom nucleophiles using polyhalomethanes has been developed. In addition, the pivotal visible light
One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates
Barham, Joshua P.,John, Matthew P.,Murphy, John A.
supporting information, p. 2981 - 2988 (2015/02/19)
Nucleophilic trapping of iminium salts generated via oxidative functionalisation of tertiary amines is well established with stabilised carbon nucleophiles. The few reports of organometallic additions have limited scope of substrate and organometallic nucleophile. We report a novel, one-pot methodology that functionalises N - substituted tetrahydroisoquinolines by visible lightassisted photooxidation, followed by trapping of the resultant iminium ions with organometallic nucleophiles. This affords 1,2-disubstituted tetrahydroisoquinolines in moderate to excellent yields.
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.
α-Substituted Phosphonates. 43. Synthesis and Reactivity of 1,2,3,4-Tetrahydroisoquinolin-1-phosphonates
Gross, H.,Ozegowski, S.
, p. 437 - 445 (2007/10/02)
N-Alkyl- and N-arylsubstituted 1,2,3,4-tetrahydroisochinolin-1-phosphonates 1 have been synthesized from the corresponding 3,4-dihydroisochinoliniumbromides 7 and triethylphosphite.The N-unsubstituted 1,2,3,4-tetrahydroisochinolin-1-phosphonate 10 is available starting from the 1,2,3,4-tetrahydroisochinolin-1-phosphonic acid by esterification with triethylformate and splitting off the formyl group of the primarily formed N-formyl derivative 14. - N-Quarternated tetrahydroisochinolines 19 and the 1-phosphorylated derivatives 17, respectively react with triethylphosphite in an unexpected way by dealkylation and not by splitting off the isochinolinring. - By Horner-synthesis with 1 the 1-aralkylidene-isochinolines 23 are available in moderate yields.
