Discovery of 1612-65-3

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An enthalpic scale of hydrogen-bond basicity. 3. Ammonia, primary, secondary, and tertiary amines

A reliable enthalpic scale of hydrogen-bond acceptor strength (basicity) is built for aliphatic amines by means of a new infrared method, from the temperature variation of hydrogen-bond equilibrium constants. Enthalpies of hydrogen bonding to a reference hydrogen-bond acceptor, 4-fluorophenol, have been determined in CCl4 and/or C2C14 for ammonia and 68 primary, secondary, and tertiary amines. The scale spans from -23.8 kJ mol -1 for i-Pr2NCH(Et)2 to -39.4 kJ mol -1 for Et3N. This large variation is mainly explained by the basicity-enhancing electronic effects of alkyl groups, which can be overcompensated by dramatic basicity-decreasing steric effects. Relationships between DeltaH and the change in electronic energy or the infrared shift of the OH stretching upon hydrogen bonding are studied and found useful in the prediction of the hydrogen bond enthalpies of amines with several hydrogen-bond acceptor sites. A careful statistical analysis of the enthalpy-entropy relationship shows an isoentropic tendency. The entropies of 65% of hydrogen-bonding reactions between aliphatic amines and 4-fluorophenol have a mean value of -55.1 ¡À 4.2 J K-1 mol-1. Amines excluded from the isoentropic set are mainly severely hindered ones. The hydrogen-bond enthalpic scale can be useful in measuring the electrostatic character of Lewis bases.

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Reference£º
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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Convenient preparation of some N-substituted 1,2,3,4-tetrahydroisoquinolines lacking electron-donating substituents

N,N-Bis(benzotriazol-1-ylmethyl)-beta-phenylethylamines 3 are cyclised intramolecularly in conc. H2SO4 to the corresponding N-benzotriazol-1-ylmethyl-1,2,3,4-tetrahydroisoquinolines 4. The remaining benzotriazolyl-moiety can be replaced by nucleophiles, leading to N-substituted 1,2,3,4-tetrahydroisoquinolines 5-8.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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Nucleophilic addition of Lewis acid complexed alpha-amino carbanions to arynes: Synthesis of 1-aryl- N -methyl-1,2,3,4-tetrahydroisoquinolines

The direct C-1 arylation of N-methyl-1,2,3,4-tetrahydroisoquinolines via coupling of alpha-amino carbanions derived from Lewis acid complexed tetrahydroisoquinolines and in situ generated arynes is described. This process provides an easy access to the title compounds and a new synthetic route to (¡À)-cryptostyline alkaloids. Georg Thieme Verlag Stuttgart New York.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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Tetrahydroisoquinolines in therapeutics: a patent review (2010-2015)

Introduction: 1,2,3,4-Tetrahydroisoquinoline (THIQ) is one of the ?privileged scaffolds?, commonly found in nature. Initially, this class of compounds was known for its neurotoxicity. Later on, 1-methyl-1,2,3,4-tetrahydroisoquinoline was proved as an endogeneous Parkinsonism-preventing agent in mammals. The fused THIQs have been studied for their role as anticancer antibiotics. The US FDA approval of the trabectedin for the treatment of soft tissue sarcomas, is a milestone in the anticancer drug discovery. Areas covered: This review covers the patents on various therapeutic activities of the THIQ derivatives in the years between 2010 and 2015. Patents were collected using a thorough search of Espacenet and WIPO databases. The therapeutic areas covered include cancer, malaria, central nervous system (CNS), cardiovascular, metabolic disorders, and so on. This also includes several patents on specific THIQs of clinical importance. Expert opinion: A large number of the THIQ derivatives have been synthesised for various therapeutic activities, with noticeable success in the area of drug discovery for cancer and CNS. They may also prove to be promising candidates for various infectious diseases, such as malaria, tuberculosis, HIV-infection, HSV-infection, leishmaniasis, etc. They can also be developed as novel class of drugs for various therapeutic activities with unique mechanism of action.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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Method for Preparting Alkylamines

The present invention relates to a method for preparing alkylamines using carbon monoxide and the use of this method in the manufacturing of vitamins, pharmaceutical products, adhesives, acrylic fibres and synthetic leathers, pesticides, surfactants, detergents and fertilisers. It also relates to a method for manufacturing vitamins, pharmaceutical products, adhesives, acrylic fibres, synthetic leathers, pesticides, surfactants, detergents and fertilisers, comprising a step of preparing alkylamines by the method according to the invention. The present invention further relates to a method for preparing marked alkylamines and uses thereof.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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Inhibition of complex I by isoquinoline derivatives structurally related to 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)

Mitochondrial respiratory failure secondary to complex I inhibition may contribute to the neurodegenerative process underlying nigral cell death in Parkinson’s disease (PD). Isoquinoline derivatives structurally related to 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) or 1-methyl-4-phenylpyridinium (MPP+) may be inhibitors of complex I, and have been implicated in the cause of PD as endogenous neurotoxins. To determine the potency and structural requirements of isoquinoline derivatives to inhibit mitochondrial function, we examined the effects of 22 neutral and quaternary compounds from three classes of isoquinoline derivatives (11 isoquinolines, 2 dihydroisoquinolines, and 9 1,2,3,4-tetrahydroisoquinolines) and MPP+ on the enzymes of the respiratory chain in mitochondrial fragments from rat forebrain. With the exception of norsalsolinol and N,n-propylisoquinolinium, all compounds inhibited complex I in a time-independent, but concentration-dependent manner, with IC50s ranging from 0.36-22 mM. Several isoquinoline derivatives were more potent inhibitors of complex I than 1-methyl-4-phenylpyridinium ion (MPP+) (IC50 = 4.1 mM), the most active being N-methyl-6-methoxy-1,2,3,4-tetrahydroisoquinoline (IC50 = 0.36 mM) and 6-methoxy-1,2,3,4-tetrahydroisoquinoline (IC50 = 0.38 mM). 1,2,3,4-Tetrahydroisoquinoline was the least potent complex I inhibitor (IC50 ~ 22 mM). At 10 mM, only isoquinoline (23.1%), 6,7-dimethoxyisoquinoline (89.6%), and N-methylsalsolinol (34.8%) inhibited (P < 0.05) complex II-III, but none of the isoquinoline derivatives inhibited complex IV. There were no clear structure-activity relationships among the three classes of isoquinoline derivatives studied, but lipophilicity appears to be important for complex I inhibition. The effects of isoquinoline derivatives on mitochondrial function are similar to those of MPTP/MPP+, so respiratory inhibition may underlie their reported neurotoxicity. One of the oldest and most widely used commercial enzyme inhibitors is aspirin, Product Details of 1612-65-3, which selectively inhibits one of the enzymes involved in the synthesis of molecules that trigger inflammation. you can also check out more blogs about 1612-65-3

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

The important role of 1612-65-3

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SODIUM HYDROGEN TELLURIDE AS A USEFUL NUCLEOPHILIC REAGENT FOR THE CLEAVAGE OF EPOXIDES AND OF QUATERNARY AMMONIUM SALTS

Sodium hydrogen telluride opens many epoxides cleanly by an SN2 process to give telluro-alcohols, which by reduction with nickel boride afford alcohols.An intermediate telluro-alcohol was converted to olefin in high yield by treatment with p-toluene-sulphonyl chloride in pyridine.Quaternary ammonium salts are also cleaved efficiently by sodium hydrogen telluride.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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Methyl-Selective alpha-Oxygenation of Tertiary Amines to Formamides by Employing Copper/Moderately Hindered Nitroxyl Radical (DMN-AZADO or 1-Me-AZADO)

Methyl-selective alpha-oxygenation of tertiary amines is a highly attractive approach for synthesizing formamides while preserving the amine substrate skeletons. Therefore, the development of efficient catalysts that can advance regioselective alpha-oxygenation at the N-methyl positions using molecular oxygen (O2) as the terminal oxidant is an important subject. In this study, we successfully developed a highly regioselective and efficient aerobic methyl-selective alpha-oxygenation of tertiary amines by employing a Cu/nitroxyl radical catalyst system. The use of moderately hindered nitroxyl radicals, such as 1,5-dimethyl-9-azanoradamantane N-oxyl (DMN-AZADO) and 1-methyl-2-azaadamanane N-oxyl (1-Me-AZADO), was very important to promote the oxygenation effectively mainly because these N-oxyls have longer life-times than less hindered N-oxyls. Various types of tertiary N-methylamines were selectively converted to the corresponding formamides. A plausible reaction mechanism is also discussed on the basis of experimental evidence, together with DFT calculations. The high regioselectivity of this catalyst system stems from steric restriction of the amine-N-oxyl interactions.

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Reference£º
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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Reactions of alkyl, benzyl and stannyl halides with Lewis acid complexed alpha-lithiated tertiary amines

alpha-amino stannanes can be obtained readily from tertiary amines through BF3 promoted deprotonation; in situ CsF treatment of BF3 complexed stannanes followed by lithium-transmetalation can be used to procure those alpha-alkylation products which are not available directly.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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Mercuric dehydrogenations of N-tertiary piperidine derivatives with different substitution pattern

A comparison of the dehydrogenation of different N-tertiary piperidine derivatives with mercuric EDTA and mercuric acetate shows an increase of the reaction with the complex method.This is especially evident with the N-demethylation of 1,2,2,6,6-pentamethylpiperidine.Generally with dehydrogenations offering a possibility of generating a tertiary or a secondary carbenium ion, the latter alternative is mostly also realized to a minor extent.

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Reference£º
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem