78317-79-0

Upstream product

• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 1765-93-1 4-fluoroboronic acid 
• 493-05-0 isochromane 
• 371-40-4 4-fluoroaniline 
• 153333-52-9 1-(2-iodoethyl)-2-(iodomethyl)benzene 

Downstream Products

• 1895-74-5 2-(4-fluorophenyl)-3,4-dihydroisoquinolin-2-ium bromide 
• 1439904-95-6 1-(1H-indol-3-yl)-2-(4-fluoro-phenyl)-1,2,3,4-tetrahydroisoquinoline 
• 1608092-60-9 C₂₅H₂₁FN₂ 
• 1391634-82-4 (S)-2-(2-(4-fluorophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)acrylaldehyde 
• 1360260-64-5 2-(2-(4-fluorophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)-1-phenylethanone 
• 1675-52-1 2-(4-fluorophenyl)-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile 

Relevant academic research and scientific papers

Phosphoryl chloride-mediated solvent-free synthesis of N-aryl-substituted azacycles from arylamines and cyclic ethers

A solvent- and metal-free protocol for preparation of N-aryl substituted azacycles from arylamines and cyclic ethers is described. In this method, the combination of POCl3 and DBU is crucial for conversion of arylamines and cyclic ethers to five- and six-membered azacycles. Without solvent, a variety of N-aryl-substituted, five-membered azacycles (pyrrolidines, 2-methylpyrrolidines, and piperidine) and six-membered azacycles (isoindolines and tetrahydroisoquinolines) are synthesized in high yields. This green method provides a sustainable and efficient approach for the preparation of azacycles from various cyclic ethers.

N-Aryl Groups Are Ubiquitous in Cross-Dehydrogenative Couplings Because They Stabilize Reactive Intermediates

The mechanism of cross-dehydrogenative coupling (CDC) reactions has been examined by experimental and computational methods. We provide a rationale for the ubiquity of the N-aryl group in these reactions. The aryl substituent stabilizes two intermediates

Synthetic method for five-component and six-component N-substituted nitrogenous heterocyclic compounds

The invention provides a synthetic method for preparing five-component and six-component N-substituted nitrogenous heterocyclic compounds from aromatic amine and five-component and six-component oxygen heterocyclic compounds via mediation by an aminotitanium intermediate. The five-component and six-component N-substituted nitrogenous heterocyclic compounds provided by the invention specifically refer to N-aryltetrahydropyrrole, N-aryl-2-methyltetrahydropyrrole, N-aryltetrahydropyrane, N-aryl-3,4-dihydro-1H-2-pyrane with a general chemical formula as defined in the specification. In the formula, Ar is a phenyl group, a 4-methylphenyl group, a 2-halophenyl group, a 3-halophenyl group or a 4-halophenyl group. The invention discloses the chemical structures and synthetic method of the compounds.

Titanium tetrachloride-mediated synthesis of N-aryl-substituted azacycles from cyclic ethers

Titanium tetrachloride-mediated transformation of five- and six-membered cyclic ethers to the corresponding N-aryl-substituted azacycles is conducted in moderate to good yields under mild reaction conditions. Computational studies suggested a mechanism involving a Lewis acid-assisted ring-opening, a seven-membered metallacycle intermediate and a ring-closing process facilitated by direct participation of the metal center.

Synthesis of N-aryl substituted, five- and six-membered azacycles using aluminum-amide complexes

Synthesis of N-aryl substituted, five- and six-membered azacycloalkanes, isoindolines and tetrahydroisoquinolines, has been described. In this synthesis, cyclic ethers (n = 1, 2) were treated with dimethylaluminum-amide reagents, derived from a range of aryl amines and trimethylaluminum, to afford the corresponding azacycles in good yields. This journal is the Partner Organisations 2014.

Synthesis of 2-aryl-3,4-dihydroisoquinolin-2-ium bromides and their in Vitro acaricidal activity against Psoroptes cuniculi

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

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.