56537-72-5

Upstream product

• 102-01-2 N-phenylacetoacetamide 
• 31844-92-5 2-chloro-N-phenyl-3-oxobutanamide 
• 60-24-2 2-hydroxyethanethiol 
• 102437-86-5 S-<2-<<1-methyl-3-oxo-3-(phenylamino)-1-propenyl>oxy>ethyl> 2-<<1-methyl-3-oxo-3-(phenylamino)-1-propenyl>oxy>ethanethiosulfinate 

Downstream Products

• 187826-51-3 2-(2-Chloro-ethylsulfanyl)-3-oxo-N-phenyl-butyramide 

Relevant academic research and scientific papers

Synthesis of New Dihydrooxathiino[2,3-b]quinoline

A synthesis of new dihydrooxathiinoquinoline 4 is described. The key compound 6 was prepared by known methods from acetoacetanilide 1. A condensation of β-chlorosulfide 6 in 75% aqueous sulfuric acid gave quinolone 5. Conversion of 5 to 4 was achieved by treatment with potassium hydroxide in ethanol solution.

CONVERSION OF DIHYDRO-1,4-OXATHIIN-3-CARBOXAMIDE TO THE ISOMERIC DIHYDRO-1,4-OXATHIIN-2-CARBOXAMIDE

The preparation of isomeric dihydro-1,4-oxathiin (3) from the dihydro-1,4-oxathin (1) via dichloro-1,4-oxathiane (4) is described.Chlorination of 1 followed by treatment of the resulting dichloride (4) with aqueous acetone gave dihydroxy-1,4-oxathiin (5).The solvolysis to produce intermediate chlorohydrin (11) was favored relative to elimination reaction to give exomethylene compound (8).Dehydration of 5 followed by reduction afforded α-hydroxy-1,3-oxathiolane (2) which is a key compound to prepare the isomeric dihydro-1,4-oxathiin (3).The reason for more facile displacement of chlorine at C-2 in comparison with that at C-4 in 4 was also discussed.