1,3-Cyclohexanedione → 1-phenyl-1,2,9,10-tetrahydro[1,4]oxazino[2,3,4-jk]carbazol-7(8H)-one

HRID 1279685Notes

Reaction equation

[C:1]1([CH:7]2[N:12](N)[C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[O:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]1(=O)[CH2:23][CH2:22][CH2:21][C:20](=[O:24])[CH2:19]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:1]1([CH:7]2[N:12]3[C:11]4[C:14]([C:19]5[C:20](=[O:24])[CH2:21][CH2:22][CH2:23][C:18]=53)=[CH:15][CH:16]=[CH:17][C:10]=4[O:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a mixture of 3-phenyl-2,3-dihydro4H-1,4-benzoxazin-4-ylamine (1.042 g, 4.6 mmol) in toluene (30 mL) is added, with stirring, cyclohexane-1,3-dione (0.538 g, 4.8 mmol). The mixture is heated to 85° C. for 15 min, at which time p-toluenesulfonic acid monohydrate (0.874 g, 4.6 mmol) is added and the temperature increased to 110° C. The mixture is refluxed for 24 h, cooled to room temperature and concentrated. The residue is partitioned between CH2Cl2/1N NaOH and the organic layer is washed with brine and dried over magnesium sulfate. Column chromatography (100 g silica gel) using (acetone/hexane (25/75)) as eluent gave 0.475g (34%) of 1-phenyl-1,2,9,10-tetrahydro[1,4]oxazino[2,3,4-jk]carbazol-7(8H)-one.

Workup

additionis added
additionis added
temperatureThe mixture is refluxed for 24 h
temperaturecooled to room temperature
concentrationconcentrated
customThe residue is partitioned between CH2Cl2/1N NaOH
washthe organic layer is washed with brine
dry with materialdried over magnesium sulfate

Sources & evidence

ORD record: ord-1b22216b48114a319f0b9852d32aa333
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06448397B1

Reaction notes

Loading…