HCID 14423247, compound → HCID 14423294, compound

Participants

Reaction Steps

By basically the same reaction but employing two equivalents of the peracid oxidant at 25° C. for 50 hrs., the corresponding sulfone, 6,7,8,9-tetrahydro-9-(3-methylsulfonylphenyl)-5H-cyclopenta[b] [1,8]naphthyridin-5-one is prepared, m.p. 271°-273°, after crystallization from CH3CN. Similarly, starting with 10-(3-chlorophenyl)-6,8,9,10-tetrahydro-5H-thiopyrano[4,3-b] [1,8]naphthyridin-5-one or 4-(3-chlorophenyl)-2,3,4,9-tetrahydrothieno[3,2-b] [1,8]naphthyridin-9-one and one equivalent of the peracid oxidant, the sulfoxides, 10-(3-chlorophenyl)-6,8,9,10-tetrahydro-5H-thiopyrano[4,3-b] [1,8]naphthyridin-5-one-7-oxide (m.p. 211°-212° C. after crystallization from CH3CN/CH3COOC2H5) or 4-(3-chlorophenyl)-2,3,4,9-tetrahydrothieno[3,2-b] [1,8]naphthyridin-9-one-1-oxide (m.p. 266°-267° C. after crystallization form CH3CN), respectively, are prepared. By employing two equivalents of the peracid oxidant, the corresponding dioxides are prepared; i.e., 10-(3-chlorophenyl)-6,8,9,10-tetrahydro-5H-thiopyrano[4,3-b] [1,8]naphthyridin-5-one-7,7-dioxide (m.p. 249°-250° C. after crystallization from CH3CN/pet. ether) and 4-(3-chlorophenyl)-2,3,4,9-tetrahydrothieno[3,2-b] [1,8]naphthyridin-9-one-1,1-dioxide (m.p. 277°-278° C. after crystallization from CHCl3 --CH3CN).

Provenance & Evidence