142266-67-9

Upstream product

• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 501-53-1 benzyl chloroformate 
• 138350-92-2 tert-butyl 1,2,3,4-tetrahydroisoquinoline-2-carboxylate 
• 100-51-6 benzyl alcohol 
• 504-31-4 pyran-2-one 
• 191545-78-5 N-benzyloxycarbonyl-N-benzyl-2-(phenylsulfinyl)ethylamine 
• 100-52-7 benzaldehyde 
• 67747-34-6 benzyl[2-(phenylsulfanyl)ethyl]amine 
• 66859-95-8 benzylidene-(2-phenylsulfanyl-ethyl)-amine 
• 14099-81-1 1,2,3,4-tetrahydroisoquinoline 
• 124-38-9 carbon dioxide 
• 191545-91-2 1,2,3,4-tetrahydro-2-benzyloxycarbonyl-4-phenylthioisoquinoline 

Downstream Products

• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 1260506-80-6 phenylmethyl-1-(1H-indol-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 1260507-08-1 2(1H)-isoquinolinecarboxylic acid-3,4-dihydro-1-(2,4,6-trimethoxyphenyl)-phenylmethyl ester 

Relevant academic research and scientific papers

Generation and regioselective trapping of a 3,4-piperidyne for the synthesis of functionalized heterocycles

We report the generation of the first 3,4-piperidyne and its use as a building block for the synthesis of annulated piperidines. Experimental and computational studies of this intermediate are disclosed, along with comparisons to the well-known 3,4-pyridyne. The distortion/interaction model is used to explain the observed regioselectivities.

Transition-Metal-Free Oxidative Cross-Coupling of Triorganoindium Reagents with Tetrahydroisoquinolines

Triorganoindium reagents (R3In) react with tetrahydroisoquinolines (THIQs) in the presence of Ph3CBF4 as an oxidant to afford 1-substituted THIQs. The reaction proceeds in good yields at rt using 50 mol % R3In with a variety of organic groups. 1H NMR studies show the generation of an iminium ion intermediate, supporting a two-step mechanism based on THIQ oxidation and R3In nucleophilic addition. This reaction was applied to the synthesis of the alkaloid nuciferine in three steps.

Aerobic α-Oxidation of N-Substituted Tetrahydroisoquinolines to Dihydroisoquinolones via Organo-photocatalysis

An efficient visible-light-induced α-oxidation of N-substituted tetrahydroisoquinolines to dihydroisoquinolones has been developed using eosin Y as an organo-photocatalyst and oxygen as a green oxidant. The reactions were carried out under mild reaction conditions; the desired dihydroisoquinolones were obtained in up to 96% yield at room temperature under oxygen atmosphere. This transformation provides a convenient route to dihydroisoquinolones with a wide range of substrates. (Figure presented.).

Thiyl radical promoted iron-catalyzed-selective oxidation of benzylic sp3 C-H bonds with molecular oxygen

A ligand-free iron-catalyzed method for the oxygenation of benzylic sp3 C-H bonds by molecular oxygen (1 atm) using a thiyl radical as a cocatalyst has been developed. This transformation provides a facile access to amides, esters and ketones from readily accessible corresponding amines, ethers and alkanes. It features high regioselectivity, mild oxidative conditions and excellent functional group compatibility, providing good opportunities to the site-selective functionalization of complex molecules. Preliminary mechanistic studies suggest that this reaction may not undergo a benzylic cation intermediate pathway and the carbonyl oxygen atom in the products may be derived from molecular oxygen.

Tropylium-Promoted Oxidative Functionalization of Tetrahydroisoquinolines

Structural modification of the tetrahydroisoquinoline (THIQ) framework is of significant interest to organic chemists due to its central role in heterocyclic and medicinal chemistry. Here we demonstrate an efficient metal-free method for the oxidative fun

A Simple, efficient, Catalyst-Free and Solvent-Less Microwave-Assisted process for N-Cbz Protection of Several amines

A simple, green and chemo-selective method for the N-benzyloxycarbonylation of amines, β-amino alcohols, α-amino esters and sulfonamides has been developed under microwave irradiation. Good to excellent yields of the N-benzyloxy-carbamates compounds were obtained in short times without any side products.

One-pot synthesis of carbamates and thiocarbamates from Boc-protected amines

A highly efficient one-pot procedure for the synthesis of carbamates and thiocarbamates has been described. In the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, the isocyanate intermediates were generated in situ for further reactions with alcohols and thiols to afford the desired carbamates and thiocarbamates in high yields.

Parallel synthesis of ureas and carbamates from amines and CO2 under mild conditions

"Chemical Equation Presented" A mild and efficient library synthesis technique has been developed for the synthesis of ureas and carbamates from carbamic acids derived from the DBU-catalyzed reaction of amines and gaseous carbon dioxide. Carbamic acids derived from primary amines reacted with Mitsunobu reagents to generate isocyanates in situ which were condensed with primary and secondary amines to afford the desired ureas. Similarly, carbamic acids from secondary amines reacted with alcohols activated with Mitsunobu reagents to form carbamates.

Affinity of?1-aryl-1,2,3,4-tetrahydroisoquinoline derivatives to?the?ion channel binding site of?the?NMDA receptor complex

A series of 1-aryl-1,2,3,4-tetrahydroisoquinoline and 8-methyl-1-aryl-1,2,3,4-tetrahydroisoquinoline derivatives was evaluated for affinity to the PCP binding site of the NMDA receptor complex. The (S)-configurated tetrahydroisoquinoline derivative (S)-4e·HCl bearing a 2-methylphenyl substituent in position 1 of the heterocyclic ring system and a methyl group in position 8 was found to exhibit the highest affinity among the derivatives with a Ki-value of 0.0374?μM. In addition, this compound shows a remarkable enantioselectivity of binding by being almost 90 times more potent than the corresponding (R)-enantiomer (R)-4e·HCl. Additionally, a convenient and efficient synthetic approach to racemic 1-aryl-1,2,3,4-tetrahydroisoquinoline derivatives is described.

Carboxylation and Mitsunobu reaction of amines to give carbamates: Retention vs inversion of configuration is substituent-dependent

(Equation Presented) A mild method for the synthesis of carbamates from amino alcohols involves sequential carboxylation with carbon dioxide, followed by a Mitsunobu reaction. Unexpectedly, the stereochemical course of the Mitsunobu reaction is dependent on whether the carbamic acid intermediate is N-substituted with hydrogen (retention) or carbon (inversion).