67747-34-6

Upstream product

• 2510-33-0 N-benzyl-2-oxazolidinone 
• 108-98-5 thiophenol 
• 66859-95-8 benzylidene-(2-phenylsulfanyl-ethyl)-amine 
• 100-39-0 benzyl bromide 
• 699-12-7 2-(phenylthio)ethanol 
• 100-52-7 benzaldehyde 
• 5535-49-9 2-Chloroethyl phenyl sulfide 
• 100-46-9 benzylamine 
• 2014-75-7 2-(phenylthio)ethanamine 

Downstream Products

• 191545-71-8 N-acetyl-N-benzyl-2-(phenylthio)ethylamine 
• 191545-72-9 N-benzyloxycarbonyl-N-benzyl-2-(phenylthio)ethylamine 
• 191545-91-2 1,2,3,4-tetrahydro-2-benzyloxycarbonyl-4-phenylthioisoquinoline 
• 191545-78-5 N-benzyloxycarbonyl-N-benzyl-2-(phenylsulfinyl)ethylamine 
• 191545-77-4 N-acetyl-N-benzyl-2-(phenylsulfinyl)ethylamine 
• 191545-79-6 N-benzyl-N-formyl-2-(phenylsulfinyl)ethylamine 
• 191545-92-3 1,2,3,4-tetrahydro-2-formyl-4-phenylthioisoquinoline 
• 142266-67-9 N-benzyloxycarbonyl-1,2,3,4-tetrahydroisoquinoline 
• 1699-52-1 2-formyl-1,2,3,4-tetrahydroisoquinoline 
• 1612-65-3 2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 866629-86-9 (2E)-N-benzyl-N-vinylbut-2-enamide 
• 191545-73-0 N-benzyl-N-formyl-2-(phenylthio)ethylamine 

Relevant academic research and scientific papers

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).

The Use of 2-Oxazolidinones as Latent Aziridine Equivalents. 2. Aminoethylation of Aromatic Amines, Phenols, and Thiophenols

The utility of 2-oxazolidinones 1 as latent, carboxylated aziridine functionalities was examined.Reaction of 2-oxazolidinone (1a), 3-methyl2-oxazolidinone (1b), 3-(phenylmethyl)-2-oxazolidinone (1c), 3-phenyl-2-oxazolidinone (1d) 4,4-dimethyl-2-oxazolidinone (1e), and 5-ethyl-2-oxazolidinone (1f) with aromatic amine salts, phenol, or thiophenols at elevated temperatures (> 130 deg C) afforded aminoethylated adducts.The aminoethylation occurred with concomitant loss of carbon dioxide to furnish variously substituted N-aryl-1,2-ethanediamines 4, 1-(2-phenoxyethyl)-2-imidazolidinone (8), or 2-(arylthio)ethanamines 9 on reactions of 1 with aromatic amine salts, phenol, and thiophenols, respectively.Imidazolidinone 8 is believed to be a secondary reaction product resulting from the condensation of the initially formed 2-phenoxyethanamine with starting oxazolidinone 1a.The aminoethylation reaction did not proceed with aliphatic amine hydrochlorides or alkyl mercaptans.Preliminary mechanistic pathways for these ring openings were also investigated employing a specific, C-5 deuterium-labeled oxazolidinone 1b-d2.Ring-opening experiments of 1b-d2 with N-methylaniline hydrochloride suggest reaction can occur through either a dioxazolinium 5 and/or 5 intermediate.In contrast, reaction of 1b-d2 with thiophenol suggests ring-opening to proceed only via the dioxazolinium pathway.