41852-27-1

Upstream product

• 22901-09-3 2-(2-bromoethyl)benzaldehyde 
• 62-53-3 aniline 
• 60-12-8 2-phenylethanol 
• 153333-52-9 1-(2-iodoethyl)-2-(iodomethyl)benzene 
• 3340-78-1 2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 493-05-0 isochromane 
• 591-50-4 iodobenzene 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 850130-95-9 1,2,3,4-tetrahydro-1-(nitromethyl)-2-phenylisoquinoline 
• 87992-94-7 1,2,3,4-tetrahydro-2-phenylisoquinolin-1-yl-1-phosphonic acid diethyl ester 
• 13355-47-0 1-phenyl-2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 59224-75-8 1-(4-methoxyphenyl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 1308790-32-0 1-(2-methylallyl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 1227403-16-8 1-allyl-2-(phenyl)-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

Visible-light photoredox catalysis in flow

Photoredox catalysis: A variety of organic transformations mediated by visible-light-active photoredox catalysts have been conducted in a photochemical flow reactor. The reactor design is very simple and can be easily implemented in any laboratory (see pi

Synthesis of α-aminonitriles using aliphatic nitriles, α-amino acids, and hexacyanoferrate as universally applicable non-toxic cyanide sources

In cyanation reactions, the cyanide source is often directly added to the reaction mixture, which restricts the choice of conditions. The spatial separation of cyanide release and consumption offers higher flexibility instead. Such a setting was used for the cyanation of iminium ions with a variety of different easy-to-handle HCN sources such as hexacyanoferrate, acetonitrile or α-amino acids. The latter substrates were first converted to their corresponding nitriles through oxidative decarboxylation. While glycine directly furnishes HCN in the oxidation step, the aliphatic nitriles derived from α-substituted amino acids can be further converted into the corresponding cyanohydrins in an oxidative C-H functionalization. Mn(OAc)2 was found to catalyze the efficient release of HCN from these cyanohydrins or from acetone cyanohydrin under acidic conditions and, in combination with the two previous transformations, permits the use of protein biomass as a non-toxic source of HCN.

Isothiourea-Catalyzed Enantioselective Addition of 4-Nitrophenyl Esters to Iminium Ions

Isothioureas catalyze the enantioselective addition of 4-nitrophenyl esters to tetrahydroisoquinoline-derived iminium ions. 4-Nitrophenoxide, generated in situ from initial N-acylation of the isothiourea by the 4-nitrophenyl ester, is used to facilitate catalyst turnover in this reaction process. Optimization showed that 4-nitrophenyl esters give the best reactivity in this protocol over a range of alternative aryl esters, with the observed enantioselectivity markedly dependent on the nature of the iminium counterion. Highest yields and enantioselectivity were obtained using iminium bromide ions generated in situ via photoredox catalysis using BrCCl3 and Ru(bpy)3Cl2 (0.5 mol %) and commercially available tetramisole (5 mol %) as the Lewis base catalyst. The scope and limitations of this procedure was developed, giving the desired β-amino amide products in up to 96% yield, 79:21 diastereomeric ratio (dr), and ermajor (2R,1′S) 99.5:0.5.

Reactions Catalysed by a Binuclear Copper Complex: Relay Aerobic Oxidation of N-Aryl Tetrahydroisoquinolines to Dihydroisoquinolones with a Vitamin B1 Analogue

N-Aryl tetrahydroisoquinolines were oxidised to dihydroisoquinolones through the relay catalysis of a binuclear paddle-wheel copper complex and a vitamin B1 analogue with oxygen as oxidant. Mechanistic studies revealed that the copper catalyst oxidises amines to the corresponding iminium salts, which are then oxygenated to lactam products by catalysis of the vitamin B1 analogue.

The Photocatalyzed Aza-Henry Reaction of N-Aryltetrahydroisoquinolines: Comprehensive Mechanism, H?- versus H+-Abstraction, and Background Reactions

The cross-dehydrogenative coupling (CDC) reaction of N-aryltetrahydroisoquinolines (THIQ) is one of the most exploited photocatalytic transformation and a test reaction for an exceptional variety of catalysts. However, its mechanism remained unclear conce

A metal-free cyclic iminium induced one-pot double annulation cascade: Access to dihydroisoquinolinium (DHIQ) salts

A reactive cyclic iminium induced one-pot Groebke-Blackburn-Bienayme (GBB) double annulation cascade (DAC) for the synthesis of skeletally diverse DHIQ salts has been described. The key features of this protocol are transition-metal and solvent-free, mild reaction conditions, robust method, one-step construction of two privileged heterocyclic rings, clean reaction profile and operational simplicity.

α-Cyanation of Aromatic Tertiary Amines using Ferricyanide as a Non-Toxic Cyanide Source

The reaction of aromatic tertiary amines with potassium ferricyanide directly provides the useful α-amino nitriles. The inexpensive iron complex functions both as an oxidant and as a cyanide source. The presence of molecular oxygen speeds up the reaction which can be performed in aqueous tert-butanol or even in ethanol-based mixtures like Tequila. While amine cyanations usually employ highly toxic cyanide sources, potassium ferricyanide is even less toxic than table salt. No expensive metal complexes are required as catalysts and the co-product of the cyanation, Prussian blue, has no known toxicity and is rather used as an antidote.

No photocatalyst required-versatile, visible light mediated transformations with polyhalomethanes

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

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.

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.