191545-97-8

Upstream product

• 191545-74-1 N-benzyloxycarbonyl-N-(3,4-dimethoxyphenyl)methyl-2-(phenylsulfinyl)ethylamine 
• 1745-07-9 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 501-53-1 benzyl chloroformate 
• 63914-27-2 [2-(3,4-dimethoxy-phenyl)-ethyl]-carbamic acid benzyl ester 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 50-00-0 formaldehyd 
• 191545-88-7 1,2,3,4-tetrahydro-2-benzyloxycarbonyl-6,7-dimethoxy-4-phenylthioisoquinoline 
• 3459-92-5 DBC 

Downstream Products

• 123279-36-7 (+/-)-1-(4-chlorophenyl)-2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)ethanol 
• 2697-38-3 benzyl (6,7-dimethoxy-1-methyl-3,4-dihydro-1H-isoquinolin)-2-carboxylate 
• 15889-93-7 (+/-)-crispine A 
• 627862-69-5 (S)-benzyl 6,7-dimethoxy-1-(2-oxoethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 627862-72-0 6,7-dimethoxy-1-(2-oxo-ethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester 
• 1455712-05-6 benzyl 6,7-dimethoxy-1-(2-oxo-2-phenylethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 

Relevant academic research and scientific papers

Pictet-Spengler reactions in multiphasic supercritical carbon dioxide/CO2-expanded liquid media. In situ generation of carbamates as a strategy for reactions of amines in supercritical carbon dioxide

Acyl-Pictet-Spengler cyclizations can be achieved in scCO 2/CO2-expanded liquid media via the in situ formation of carbamate derivatives of β-arylethylamines. The Royal Society of Chemistry 2005.

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.

DDQ-promoted mild and efficient metal-free oxidative α-cyanation of N-acyl/sulfonyl 1,2,3,4-tetrahydroisoquinolines

A mild and highly efficient metal-free oxidative α-cyanation of N-acyl/sulfonyl 1,2,3,4-tetrahydroisoquinolines (THIQs) has been accomplished at an ambient temperature via DDQ oxidation and subsequent trapping of N-acyl/sulfonyl iminium ions with (n-Bu)s

A facile method for the preparation of MOM-protected carbamates

(Chemical Equation Presented) A novel method for the preparation of MOM-protected carbamates is described that avoids the use of MOM-Cl, a regulated carcinogen. The two-step, one-pot procedure generates a reactive N-chloromethyl carbamate that is quenched

An improved synthesis of 1,2,3,4-tetrahydroisoquinolines via intramolecular cyclization of N-acyl-N-(aryl)methyl-2- (phenylsulfinyl)ethylamine by Pummerer reaction

Pummerer reaction of the sulfoxides 5 of N-acyl-N-(aryl)methyl-2- (phenylthio)ethylamines (4) on treatment with trifluoroacetic anhydride (TFAA) effectively caused intramolecular cyclization under a mild condition to give N-acyl-4-phenylthin-1,2,3,4-tetrahydroisoquinolines (TIQs) (7). The reaction of the N-formyl sulfoxide 5c without a methoxy group in the benzene ring using a formyl group for N-protection is particularly efficient. Treatment of the N-formyl sulfoxide 5f with TFAA did not give away TIQ, but a sequential treatment using TFAA and BF3·Et2O afforded N-formyl-4- phenylthio-TIQ (7f) in quantitative yield. The efficiency of this method or preparing TIQs was demonstrated in the synthesis of 1,4-dideuterio-TQ (10D) and its N-methyl derivative (11D).