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Benzomorpholine Chemical Properties Boiling point 85°C/0.75mm density 1.095±0.06 g/cm3(Predicted) refractive index 1.60 pka 4.37±0.20(Predicted) Water Solubility Sparingly soluble in water.(0.26 g/L) (25°C),
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1-(2H-benzo[b][1,4]oxazin-4(3H)-yl)ethanone
1,4-benzoxazine
Conditions | Yield |
---|---|
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at -40℃; for 1.16667h; | 100% |
With sodium triethylborohydride In tetrahydrofuran at 80℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube; | 81% |
With sodium triethylborohydride In tetrahydrofuran at 80℃; for 6h; Inert atmosphere; Schlenk technique; High pressure; Sealed tube; | 81% |
(2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)(phenyl)methanone
A
1,4-benzoxazine
B
benzaldehyde
Conditions | Yield |
---|---|
With sodium bis(2-methoxyethoxy)aluminium dihydride In ethyl acetate; benzene at -40℃; | A 100% B 100% |
2-(2-aminophenoxy)ethan-1-ol
1,4-benzoxazine
Conditions | Yield |
---|---|
With [RuCl2(N-heterocyclic carbene)(bis[2-(diphenylphosphino)ethyl]amine)]; hydrogen; caesium carbonate In toluene; butan-1-ol at 120℃; under 22502.3 Torr; for 6h; Schlenk technique; Autoclave; | 100% |
Conditions | Yield |
---|---|
With [RuCl2(N-heterocyclic carbene)(bis[2-(diphenylphosphino)ethyl]amine)]; hydrogen; caesium carbonate In toluene; butan-1-ol at 120℃; under 22502.3 Torr; for 6h; Schlenk technique; Autoclave; | 98% |
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; | 92% |
Stage #1: 3,4-dihydro-3-oxo-2H-1,4-benzoxazine With lithium aluminium tetrahydride In tetrahydrofuran Heating / reflux; Stage #2: With sodium hydroxide; water In tetrahydrofuran | 79% |
1-(2H-benzo[b][1,4]oxazin-4(3H)-yl)ethanone
A
4-ethyl-3,4-dihydro-2H-benzo[b][1,4]oxazine
B
1,4-benzoxazine
Conditions | Yield |
---|---|
With triethyl borane; Triethoxysilane; sodium hydroxide In hexane at 80℃; for 6h; Reagent/catalyst; Solvent; Inert atmosphere; Sealed tube; | A 7% B 90% |
With Triethoxysilane; sodium triethylborohydride In hexane at 80℃; for 6h; Schlenk technique; Glovebox; Sealed tube; Inert atmosphere; | A 90% B n/a |
With Triethoxysilane; sodium triethylborohydride In hexane at 80℃; for 6h; Inert atmosphere; Schlenk technique; High pressure; Sealed tube; | A 90% B n/a |
2-(2-nitrophenoxy)acetonitrile
1,4-benzoxazine
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen; toluene-4-sulfonic acid In ethanol at 50℃; under 37503.8 Torr; for 2h; | 88% |
With polymethylhydrosiloxane; palladium dihydroxide In ethanol at 20℃; for 0.5h; | 73% |
2-<(2-bromophenyl)amino>ethanol
1,4-benzoxazine
Conditions | Yield |
---|---|
With racemic-2-(di-tert-butylphosphino)-1,1′-binaphthyl; palladium diacetate; caesium carbonate In toluene at 50℃; for 24h; | 87% |
With racemic-2-(di-tert-butylphosphino)-1,1′-binaphthyl; palladium diacetate; caesium carbonate In toluene at 50℃; for 24h; | 87% |
4-(p-toluenesulfonyl)-3,4-dihydro-2H-benzoxazine
1,4-benzoxazine
Conditions | Yield |
---|---|
With naphthalene; tetraethylammonium bromide In N,N-dimethyl-formamide at 0℃; Inert atmosphere; Electrolysis; | 87% |
1,4-benzoxazine
Conditions | Yield |
---|---|
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; trifluoroacetic acid In 2,2,2-trifluoroethanol at 0 - 20℃; for 17h; regioselective reaction; | 82% |
With Rh2(esp)2; trifluoroacetic acid In 2,2,2-trifluoroethanol at 20℃; for 17h; Inert atmosphere; | 82% |
benzofuran-3(2H)-one oxime
1,4-benzoxazine
Conditions | Yield |
---|---|
Stage #1: benzofuran-3(2H)-one oxime With diisobutylaluminium hydride In hexane; dichloromethane at 0 - 20℃; Inert atmosphere; Stage #2: With sodium fluoride In hexane; dichloromethane; water at 0℃; for 0.5h; | 80% |
Stage #1: benzofuran-3(2H)-one oxime With diisobutylaluminium hydride In hexane; dichloromethane at 0 - 20℃; Inert atmosphere; Stage #2: With water; sodium fluoride In hexane; dichloromethane at 0℃; for 0.5h; Inert atmosphere; regioselective reaction; | 80% |
With diisobutylaluminium hydride In dichloromethane at 0 - 20℃; | 80% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 125℃; for 15h; | 73% |
With potassium carbonate In N,N-dimethyl-formamide at 125℃; for 15h; | 65% |
With potassium carbonate In dimethyl sulfoxide at 80℃; | 62% |
Conditions | Yield |
---|---|
Stage #1: 2-amino-phenol With sodium hydride In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: (2-bromoethyl)(diphenyl)sulfonium trifluoromethanesulfonate In dichloromethane at 25 - 30℃; for 15h; Inert atmosphere; | 68% |
2-allyloxy-1-nitrobenzene
A
1,4-benzoxazine
B
4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine
Conditions | Yield |
---|---|
Stage #1: 2-allyloxy-1-nitrobenzene With ozone In methanol at -78℃; Stage #2: With hydrogen; nitrobenzene; palladium on activated charcoal In methanol at 25℃; under 3040 Torr; for 6h; | A 66% B n/a |
1-(2-chloroethoxy)-2-nitrobenzene
1,4-benzoxazine
Conditions | Yield |
---|---|
Stage #1: 1-(2-chloroethoxy)-2-nitrobenzene With platinum(IV) oxide; hydrogen; sodium acetate In ethyl acetate at 25℃; under 7500.75 Torr; for 2h; Stage #2: With triethylamine; sodium iodide In ethyl acetate for 16h; Reflux; | 37% |
4-acetyl-4H-1,4-benzoxazine
A
4-ethyl-3,4-dihydro-2H-benzo[b][1,4]oxazine
B
1,4-benzoxazine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; hydrogen; palladium on activated charcoal 1.) Et2O, 20 deg C, 30 min, 2.) ethanol; Yield given. Multistep reaction. Yields of byproduct given; |
1,4-benzoxazine
Conditions | Yield |
---|---|
With sodium hydroxide |
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 80℃; for 8h; Title compound not separated from byproducts; |
2-(2-chlorophenoxy)ethylamine
1,4-benzoxazine
Conditions | Yield |
---|---|
With sodium hydride; tert-butyl alcohol; 1,3-bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene monohydrochloride; palladium diacetate In 1,4-dioxane for 4h; |
4-(tert-butoxycarbonyl)-3,4-dihydro-2H-1,4-benzoxazine
1,4-benzoxazine
Conditions | Yield |
---|---|
With hydrogenchloride In acetonitrile | |
Stage #1: 4-(tert-butoxycarbonyl)-3,4-dihydro-2H-1,4-benzoxazine With trifluoroacetic acid In dichloromethane at 20℃; Stage #2: With sodium hydrogencarbonate In dichloromethane; water |
1-(2-bromoethoxy)-2-chlorobenzene
1,4-benzoxazine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: NaN3 / dimethylformamide / 2.5 h / 110 °C 2.1: PPh3 / tetrahydrofuran / 15 h / 20 °C 2.2: 63 percent / H2O / tetrahydrofuran / 3 h / 20 °C 3.1: N,N'-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene*HCl; NaH; t-BuOH / Pd(OAc)2 / dioxane / 4 h View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: aq. NaOH / 6 h / 100 °C 2.1: NaN3 / dimethylformamide / 2.5 h / 110 °C 3.1: PPh3 / tetrahydrofuran / 15 h / 20 °C 3.2: 63 percent / H2O / tetrahydrofuran / 3 h / 20 °C 4.1: N,N'-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene*HCl; NaH; t-BuOH / Pd(OAc)2 / dioxane / 4 h View Scheme |
1-(2-azidoethoxy)-2-chlorobenzene
1,4-benzoxazine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: PPh3 / tetrahydrofuran / 15 h / 20 °C 1.2: 63 percent / H2O / tetrahydrofuran / 3 h / 20 °C 2.1: N,N'-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene*HCl; NaH; t-BuOH / Pd(OAc)2 / dioxane / 4 h View Scheme |
N-(2-(tert-butyldimethylsiloxy)-ethyl)-2-bromoaniline
1,4-benzoxazine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 96 percent / TBAF / tetrahydrofuran / 1 h 2: 87 percent / Pd(OAc)2; Cs2CO3; 2-(di-tert-butylphosphanyl)-1,1'-binaphthyl / toluene / 24 h / 50 °C View Scheme | |
Multi-step reaction with 2 steps 1: 96 percent / TBAF / tetrahydrofuran / 1 h 2: 87 percent / Pd(OAc)2; di-tert-butyl-[2-(1,1'-binnaphthyl)]phosphine; Cs2CO3 / toluene / 24 h / 50 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate; N-benzyl-N,N,N-triethylammonium chloride / chloroform / 11 h / 0 - 55 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Reflux 2.2: 0 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium carbonate / water; tetrahydrofuran / 1 h / -10 °C 2: potassium tert-butylate / dichloromethane; isopropyl alcohol / 1 h / 0 - 20 °C 3: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 20 h / Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 80 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: methanesulfonic acid; sodium azide / 1.25 h / 0 - 20 °C 2: lithium aluminium tetrahydride / diethyl ether; tetrahydrofuran / 16 h / Reflux View Scheme |
N-(2-hydroxyphenyl)-2-chloroacetamide
1,4-benzoxazine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium tert-butylate / dichloromethane; isopropyl alcohol / 1 h / 0 - 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 - 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: acetic acid; iron / ethanol; water 2: potassium carbonate / acetonitrile / 20 h / Reflux 3: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 16 h / 120 °C 2.1: toluene-4-sulfonic acid; palladium 10% on activated carbon; hydrogen / 1,4-dioxane / 25 - 100 °C / 22502.3 Torr 2.2: 2 h / 50 °C / 30003 Torr View Scheme | |
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 2.5 h / Reflux 2.1: hydrogen; platinum(IV) oxide; sodium acetate / ethyl acetate / 2 h / 25 °C / 7500.75 Torr 2.2: 16 h / Reflux View Scheme |
1-(2-bromoethoxy)-2-nitrobenzene
1,4-benzoxazine
Conditions | Yield |
---|---|
Stage #1: 1-(2-bromoethoxy)-2-nitrobenzene With platinum(IV) oxide; hydrogen; sodium acetate In ethyl acetate at 25℃; under 7500.75 Torr; for 18h; Stage #2: With triethylamine In ethyl acetate for 6h; Reflux; |
2,2-Diethoxy-1-(o-nitrophenoxy)ethan
1,4-benzoxazine
Conditions | Yield |
---|---|
Stage #1: 2,2-Diethoxy-1-(o-nitrophenoxy)ethan With palladium 10% on activated carbon; hydrogen; toluene-4-sulfonic acid In 1,4-dioxane at 25 - 100℃; under 22502.3 Torr; Stage #2: With hydrogenchloride; hydrogen In 1,4-dioxane; water at 50℃; under 30003 Torr; for 2h; |
1,4-benzoxazine
chloroacetyl chloride
2-chloro-1-(2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)ethan-1-one
Conditions | Yield |
---|---|
With pyridine In benzene Ambient temperature; | 100% |
With triethylamine In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; | 76% |
With TEA In chloroform at 20℃; for 18h; |
1,4-benzoxazine
ethyl bromoacetate
(2,3-dihydro-benzo[1,4]oxazin-4-yl)-acetic acid ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 125℃; | 99% |
3-chlorothiophene
1,4-benzoxazine
Conditions | Yield |
---|---|
With 2-dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl; potassium carbonate; ruphos In tert-Amyl alcohol at 110℃; for 20h; Schlenk technique; Inert atmosphere; | 98% |
With 2-dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl; potassium carbonate; ruphos In tert-Amyl alcohol at 110℃; for 20h; Inert atmosphere; | 98% |
1,4-benzoxazine
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine; potassium iodide In acetonitrile at 120℃; for 4h; Microwave irradiation; | 98% |
Conditions | Yield |
---|---|
With C38H38N4O2Rh(1+)*F6P(1-) In acetonitrile at 20℃; for 17h; Mannich Aminomethylation; enantioselective reaction; | 96% |
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere; | 95% |
ammonium formate
1,4-benzoxazine
Conditions | Yield |
---|---|
In acetonitrile for 12h; Formylation; | 93% |
1,4-benzoxazine
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine; potassium iodide In acetonitrile at 120℃; for 4h; Microwave irradiation; | 93% |
Conditions | Yield |
---|---|
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In chloroform at 25℃; for 12h; Inert atmosphere; Sealed tube; | 93% |
dichloroacethyl chloride
1,4-benzoxazine
N-dichloroacetyl-3,4-dihydro-2H-1,4-benzoxazine
Conditions | Yield |
---|---|
With sodium carbonate In benzene at 25℃; | 92% |
carbon dioxide
1,4-benzoxazine
4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine
Conditions | Yield |
---|---|
With cyclopentadienyl iron(II) dicarbonyl dimer; phenylsilane; triphenylphosphine In acetonitrile at 100℃; under 760.051 Torr; for 36h; Schlenk technique; Sealed tube; | 92% |
With diphenylsilane; [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene In N,N-dimethyl-formamide at 50℃; under 760.051 Torr; chemoselective reaction; | 64% |
Conditions | Yield |
---|---|
With ammonium hexafluorophosphate; dodecacarbonyl-triangulo-triruthenium In benzene at 95℃; for 24h; | 90% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 6h; | 89.7% |
2,3-epoxy-3-phenyl-1-propanol
1,4-benzoxazine
Conditions | Yield |
---|---|
With tungsten hexa-ethoxide In acetonitrile at 55℃; for 24h; stereospecific reaction; | 89% |
1,4-benzoxazine
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 2h; | 88% |
1,4-benzoxazine
Conditions | Yield |
---|---|
at 135℃; for 12h; | 87% |
at 135℃; for 12h; | 87% |
1,4-benzoxazine
benzenesulfonyl chloride
4-(phenylsulfonyl)-3,4-dihydro-2Hbenzo[b][1,4]oxazine
Conditions | Yield |
---|---|
With triethylamine In benzene at 20℃; for 12h; Inert atmosphere; | 87% |
1,1,1,3',3',3'-hexafluoro-propanol
1,4-benzoxazine
2-(3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol
Conditions | Yield |
---|---|
With piperidin-1-yl benzoate; copper(II) acetate tetrahydrate at 70℃; for 5h; | 87% |
With [2,2]bipyridinyl; oxygen; copper(II) bis(trifluoromethanesulfonate); sodium carbonate at 50℃; under 760.051 Torr; for 3.5h; Schlenk technique; Green chemistry; regiospecific reaction; | 63% |
C15H12FNO2
1,4-benzoxazine
1-(3,4-dihydro-2H-1,4-benzoxazin-4-yl)-3-(6-fluoro-9H-carbazol-2-yloxy)-2-propanol
Conditions | Yield |
---|---|
In isopropyl alcohol Reflux; | 86% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 6h; Cooling with ice; | 86% |
Conditions | Yield |
---|---|
With 9-(2-chlorophenyl)acridine; di-tert-butyl peroxide; copper(II) hexafluoroacetylacetonate at 35℃; for 36h; Inert atmosphere; Irradiation; | 86% |
Conditions | Yield |
---|---|
With cyclopentadienyl iron(II) dicarbonyl dimer; tributylphosphine; phenylsilane In acetonitrile at 30℃; under 760.051 Torr; for 24h; Schlenk technique; Sealed tube; | 85% |
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