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7-methyl-2,4-dihydrospiro[benzo[b][1,4]dioxepine-3,2'-[1,3]dioxolane]
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
Conditions | Yield |
---|---|
With sulfuric acid In acetone for 6h; Reagent/catalyst; Solvent; Reflux; | 95% |
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
Conditions | Yield |
---|---|
With sodium nitrite In water; acetonitrile at 40℃; for 10h; | 94% |
(±)-7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-ol
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
Conditions | Yield |
---|---|
With potassium hydroxide; potassium permanganate for 2.5h; | 87% |
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
Conditions | Yield |
---|---|
With sodium carbonate; potassium iodide In acetone for 4h; Heating / reflux; | 84.45% |
1,3-Dichloroacetone
4-methyl-1,2-dihydroxybenzene
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
Conditions | Yield |
---|---|
With sodium carbonate; potassium iodide In butanone for 4.16667h; Heating / reflux; | 76.24% |
With sodium carbonate; potassium iodide In cyclohexanone for 4.41667h; Heating / reflux; | 75.25% |
With sodium carbonate; potassium iodide In acetone for 12h; Heating / reflux; | 59.91% |
1,3-dibromoroacetone
4-methyl-1,2-dihydroxybenzene
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
Conditions | Yield |
---|---|
With sodium carbonate; potassium iodide In acetone for 12h; Heating / reflux; | 69.95% |
2,2'-[(4-methyl-1,2-phenylene)bis(oxy)]bis[acetic acid] dimethyl ester
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
Conditions | Yield |
---|---|
Stage #1: 2,2'-[(4-methyl-1,2-phenylene)bis(oxy)]bis[acetic acid] dimethyl ester With potassium tert-butylate In tetrahydrofuran at 70℃; for 0.5h; Dieckmann cyclisation; Stage #2: With hydrogenchloride In ethanol; water for 0.0666667h; microwave irradiation; | |
Stage #1: 2,2'-[(4-methyl-1,2-phenylene)bis(oxy)]bis[acetic acid] dimethyl ester With potassium tert-butylate In tetrahydrofuran at 70℃; for 0.5h; Stage #2: With hydrogenchloride In ethanol at 90℃; for 2h; Further stages.; | 0.59 g |
Stage #1: 2,2'-[(4-methyl-1,2-phenylene)bis(oxy)]bis[acetic acid] dimethyl ester With potassium tert-butylate In tetrahydrofuran at 70℃; for 0.5h; Dieckmann Condensation; Inert atmosphere; Stage #2: With hydrogenchloride In ethanol; water at 120℃; for 8h; |
3,4-dihydro-7-methyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-1,5-benzodioxepine
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 76 percent / vanadium pentoxide; aq. H2O2 / acetonitrile / 70 °C 2: 87 percent / aq. KOH; KMnO4 / 2.5 h View Scheme |
4-methyl-1,2-dihydroxybenzene
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 83 percent / K2CO3 / dimethylformamide / 0.07 h / microwave irradiation 2.1: tBuOK / tetrahydrofuran / 0.5 h / 70 °C 2.2: 0.59 g / aq. HCl / ethanol / 2 h / 90 °C View Scheme | |
Multi-step reaction with 2 steps 1: potassium hydroxide; ammonium iodide / acetone; ethanol / 4 h / Reflux 2: sulfuric acid / acetone / 6 h / Reflux View Scheme | |
Multi-step reaction with 2 steps 1: potassium hydroxide; potassium iodide / ethanol; water / 4 h / Reflux 2: sulfuric acid / acetone / 6 h / Reflux View Scheme |
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; sodium acetate In water; acetonitrile at 50℃; for 24h; | 94% |
With hydroxylamine hydrochloride; sodium acetate In water; acetonitrile at 50℃; for 24h; | 90% |
With hydroxylamine hydrochloride |
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
(±)-7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-ol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether at 25℃; for 1h; Inert atmosphere; | 92% |
With hydrogen In methanol at 100℃; under 30003 Torr; for 12h; Autoclave; | 91.2% |
With sodium tetrahydroborate In methanol; water at 20℃; for 4h; | 89% |
With sodium tetrahydroborate In ethanol for 1h; Reflux; | 80% |
3-chlorophenyl-isothiocyanate
cyanoacetic acid amide
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
C20H16ClN3O3S
Conditions | Yield |
---|---|
Stage #1: 3-chlorophenyl-isothiocyanate; cyanoacetic acid amide With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one With acetic acid In N,N-dimethyl-formamide at 80℃; for 0.133333h; Microwave irradiation; | 90% |
phenyl isothiocyanate
cyanoacetic acid amide
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
C20H17N3O3S
Conditions | Yield |
---|---|
Stage #1: phenyl isothiocyanate; cyanoacetic acid amide With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one With acetic acid In N,N-dimethyl-formamide at 80℃; for 0.133333h; Microwave irradiation; | 89% |
4-fluorophenyl isothiocyanate
cyanoacetic acid amide
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
C20H16FN3O3S
Conditions | Yield |
---|---|
Stage #1: 4-fluorophenyl isothiocyanate; cyanoacetic acid amide With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one With acetic acid In N,N-dimethyl-formamide at 80℃; for 0.133333h; Microwave irradiation; | 89% |
4-Chlorophenyl isothiocyanate
cyanoacetic acid amide
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
C20H16ClN3O3S
Conditions | Yield |
---|---|
Stage #1: 4-Chlorophenyl isothiocyanate; cyanoacetic acid amide With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one With acetic acid In N,N-dimethyl-formamide at 80℃; for 0.133333h; Microwave irradiation; | 87% |
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
Conditions | Yield |
---|---|
With sodium bromate; sodium disulfite In cyclohexane; water at 50℃; for 8h; | 85% |
Cyanothioacetamide
phenyl isothiocyanate
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
C20H17N3O2S2
Conditions | Yield |
---|---|
Stage #1: Cyanothioacetamide; phenyl isothiocyanate With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one With acetic acid In N,N-dimethyl-formamide at 80℃; for 0.133333h; Microwave irradiation; | 82% |
Benzyl isothiocyanate
cyanoacetic acid amide
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
C21H19N3O3S
Conditions | Yield |
---|---|
Stage #1: Benzyl isothiocyanate; cyanoacetic acid amide With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one With acetic acid In N,N-dimethyl-formamide at 80℃; for 0.133333h; Microwave irradiation; | 81% |
isothiocyanatocyclohexane
cyanoacetic acid amide
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
C20H23N3O3S
Conditions | Yield |
---|---|
Stage #1: isothiocyanatocyclohexane; cyanoacetic acid amide With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one With acetic acid In N,N-dimethyl-formamide at 80℃; for 0.133333h; Microwave irradiation; | 80% |
trimethyl orthoformate
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
Conditions | Yield |
---|---|
With methanol; trifluorormethanesulfonic acid In nitromethane at 100℃; for 3h; | 72% |
malononitrile
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
2-(7-methyl-2H-benzo[b][1,4]dioxepin-3(4H)-ylidene)malononitrile
Conditions | Yield |
---|---|
With piperidine; acetic acid In benzene Reflux; | 52% |
ethylene glycol
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
7-methyl-2,4-dihydrospiro[benzo[b][1,4]dioxepine-3,2'-[1,3]dioxolane]
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 12h; Reflux; | 45% |
trimethyleneglycol
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
7-methyl-2,4-dihydrospiro[benzo[b][1,4]dioxepine-3,2'-[1,3]dioxane]
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 12h; Reflux; | 38% |
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 89 percent / NaBH4 / H2O; methanol / 4 h / 20 °C 2: 88 percent / Et3N / diethyl ether / 2 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / diethyl ether / 1 h / 25 °C / Inert atmosphere 2: pyridine / 2 h / 100 °C / Inert atmosphere View Scheme |
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 89 percent / NaBH4 / H2O; methanol / 4 h / 20 °C 2: 44 percent / Et3N / diethyl ether / 2 h / 20 °C View Scheme |
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 89 percent / NaBH4 / H2O; methanol / 4 h / 20 °C 2: 22 percent / Et3N / diethyl ether / 2 h / 20 °C View Scheme |
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 94 percent / hydroxylamine hydrochloride; AcONa / acetonitrile; H2O / 24 h / 50 °C 2: 54 percent / NaBH4; TiCl4 / 1,2-dimethoxy-ethane / 24 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium acetate / water; acetonitrile / 24 h / 50 °C 2: sodium tetrahydroborate; titanium tetrachloride / diethyl ether / 24 h / 20 °C / Inert atmosphere View Scheme |
ethyl 2-cyanoacetate
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
A
cis-ethyl-2-cyano-2-(7-methyl-2H-benzo[b][1,4]dioxepin-3(4H)-ylidene)acetate
Conditions | Yield |
---|---|
With piperidine; acetic acid In benzene Reflux; |
4-(N,N-dibutylamino)benzaldehyde
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
7-methyl-2,4-bis[1-(4-dibutylaminophenyl)meth-(Z)-ylidene]benzo[b]-1,4-dioxepin-3-one
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol at 50℃; for 40h; | 1.45 g |
asaraldehyde
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
7-methyl-2,4-bis[1-(2,4,5-trimethoxyphenyl)meth-(Z)-ylidene]benzo[b]-1,4-dioxepin-3-one
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol at 40℃; for 2h; | 1.45 g |
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