57342-58-2

Upstream product

• 56535-86-5 3-phenyl-1,3-oxazinan-2-one 
• 930-69-8 sodium thiophenolate 
• 108-98-5 thiophenol 
• 4911-65-3 3-chloropropyl phenyl sulfide 
• 62-53-3 aniline 
• 24536-40-1 3-phenylthiopropanol 

Downstream Products

• 250156-18-4 N-phenyl-N-(3-phenylthiopropyl)formamide 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 491-34-9 N-methyl-1,2,3,4-tetrahydroquinoline 
• 250156-27-5 N-phenyl-N-(3-phenylsulfinylpropyl)formamide 
• 250156-34-4 1-formyl-1,2,3,4-tetrahydro-4-phenylthioquinoline 

Relevant academic research and scientific papers

A novel synthesis of 1,2,3,4-tetrahydroquinolines via Pummerer-type reaction of N-aryl-N-[(phenylsulfinyl)propyl]formamide

A synthesis of 1,2,3,4-tetrahydroquinolines (TQs) 13 with two and three methoxyl groups on the benzene ring, was achieved via intramolecular cyclization of N-aryl-N-[(phenylsulfinyl)propyl]formamides 7 utilizing the Pummerer reaction as a key step. The reaction was carried out by using trifluoroacetic anhydride (TFAA) (method A) or TFAA-BF3 · Et2O (method B). The cyclization to 4-PhSTQs 8 proceeded effectively when the reaction center at the benzene ring was electronically activated by a methoxyl group. In the reaction of sulfoxide 7e having two OMe groups in the ortho- and para- positions, a different cyclization reaction leading to 1,5-benzothiazepine derivative 9 was observed, indicating that the high nucleophilicity of the benzene ring caused the unexpected reaction prior to cyclization to 4-PhSTQs 8. This route starting from methoxyanilines provides an efficient and convenient method of TQ synthesis.