Tetrahydrofuran → 3-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehyde

HRID 734217Notes

Reaction equation

HRID 734217 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[S:7][CH2:8][C:9](=[O:13])[NH:10][C:11]=2[N:12]=1.C1COCC1>ClCCl.[O-2].[O-2].[Mn+4]>[O:13]=[C:9]1[CH2:8][S:7][C:6]2[CH:5]=[CH:4][C:3]([CH:2]=[O:1])=[N:12][C:11]=2[NH:10]1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 116080936-(Hydroxymethyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one

Product 1

HCID 115935913-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehydeYield 55.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-hydroxymethyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine (330 mg) in dichloromethane (30 mL)/THF (30 mL) was treated with manganese dioxide (730 mg) and stirred at room temperature. Further manganese dioxide was added after 1 h (730 mg) and 16 h (300 mg). After a total of 20 h the mixture was filtered through kieselguhr and the filtrate evaporated. The product was triturated with EtOAc/hexane (1:1) and collected to give a solid (180 mg); LC/MS (APCI−) m/z 195 ([M−H]−, 95%), 165 (100%).

Workup

  1. filtrationAfter a total of 20 h the mixture was filtered through kieselguhr
  2. customthe filtrate evaporated
  3. customThe product was triturated with EtOAc/hexane (1:1)
  4. customcollected

Sources & evidence

ORD record
ord-670ea82f9163465db097e0ef7b514d9d
Source dataset
uspto-grants-2009_09
Patent number
US07592334B2

Reaction notes

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