HCID 14423247, compound → HCID 14423294, compound

HRID 1756241Notes

Reaction equation

HRID 1756241 reaction equation
ClC1C=C(N2C3N=CC=CC=3C(=O)C3CSCCC2=3)C=CC=1.ClC1C=C(N2C3N=CC=CC=3C(=O)C3SCCC2=3)C=CC=1.Cl[C:45]1[CH:46]=[C:47]([N:51]2[C:60]3[N:59]=[CH:58][CH:57]=[CH:56][C:55]=3[C:54](=[O:61])[C:53]3[CH2:62]S(=O)[CH2:64][CH2:65][C:52]2=3)[CH:48]=[CH:49][CH:50]=1.ClC1C=C(N2C3N=CC=CC=3C(=O)C3S(=O)CCC2=3)C=CC=1.ClC1C=C(N2C3N=CC=CC=3C(=O)C3[CH2:107][S:108](=[O:112])(=[O:111])CCC2=3)C=CC=1.ClC1C=C(N2C3N=CC=CC=3C(=O)C3S(=O)(=O)CCC2=3)C=CC=1>>[CH3:107][S:108]([C:45]1[CH:46]=[C:47]([N:51]2[C:60]3[N:59]=[CH:58][CH:57]=[CH:56][C:55]=3[C:54](=[O:61])[C:53]3[CH2:62][CH2:64][CH2:65][C:52]2=3)[CH:48]=[CH:49][CH:50]=1)(=[O:112])=[O:111]

Participants

7

Reactant 6

HCID 14423247HCID 14423247, compoundHCID 14423248HCID 14423248, compoundHCID 14423295HCID 14423295, compoundHCID 14423296HCID 14423296, compoundHCID 14423297HCID 14423297, compoundHCID 14423298HCID 14423298, compound

Product 1

HCID 14423294HCID 14423294, compound

Procedure

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 CHCl3CH3CN).

Workup

  1. customBy basically the same reaction
  2. customat 25° C.
  3. customfor 50 hrs
  4. customafter crystallization from CH3CN

Sources & evidence

ORD record
ord-16ad3cb7b40644dbbb3077805c236e10
Source dataset
uspto-grants-1995_08
Patent number
US05439916

Reaction notes

Loading…