128100-04-9

Upstream product

• 50634-27-0 1,4-dithiino[2,3-c:5,6-c']diquinoline 
• 100-44-7 benzyl chloride 
• 5188-07-8 sodium thiomethoxide 
• 146331-29-5 3',4-dibenzylthio-3,4'-diquinolinyl sulfide 
• 50634-26-9 isothioquinanthrene 
• 3492-64-6 sodium benzylmercaptide 
• 74575-24-9 X-ray structure of 3',4-dimethylthio-3,4'-diquinolinyl sulfide 

Relevant academic research and scientific papers

The 1,4-dithiin ring opening in isothioquinanthrene

The 1,4-dithiin ring opening reactions in isothioquinanthrene 1 (1,4-dithiino[2,3-c;6,5-c']diquinoline) with selected S-, O and Se-nucleophiles in DMSO or DMF at 20-70°C proceeded with cleavage of only one C4-quinolinyl - S bond to give alkali metal salts of 4-substiluted 4′-mercapto-3,3′-diquinolinyl Sulfides 2a-2h and 6 as primary products and after S-alkylation in aqueous sodium hydroxide solution 4-substituted 4′-alkylthio-3,3′-diquinolinyl Sulfides 3-5 and 7 as the final products. In contrast to sulfides 2a-2h sulfide 3a reacted with S-nucleophiles (sodium alkanethiolates) with cleavage of the C3-quinolinyl - S, C4-quinolinyl - S and CH3 - S bonds to form 3,4-dialkylthioquinolines 8a-8e as the main compounds. In the case of relatively bulky S-nucleopbiles (the 2-methyl-2-propanethiolate and to some extent the ethanethiolate anions) the cleavage of the C3-quinolinyl - S by a vicarious nucleophile (the methanethiolate anion, liberated in the cleavage of the C4-quinolinyl - S bond) was observed.

Reactions of thioquinanthrene with alkanethiolates. The Smiles rearran of diquinolinyl sulfides

Reactions of thioquinanthrene 1 with alkali metal alkanethiolates in DMSO or DMF at 70 deg proceeded through a stage of the S-S type of the Smiles rearrangement (3'-quinolinethiolate 2A - 4'-quinolinethiolate 3A) to give 4,4'-dialkylthio-3,3;-diquinolinyl