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ethyl bromide
6,7-methylenedioxy-4(1H)-oxo-cinnolin-3-carboxylic acid ethylester
Aliquat 336
cinoxacin
Conditions | Yield |
---|---|
With sodium hydroxide; potassium carbonate In water; toluene |
cinoxacin
ethanol
Conditions | Yield |
---|---|
With sodium methylate In methanol for 2h; Reflux; | 92.9% |
cinoxacin
dimethyl sulfoxide
B
{Ni(1-ethyl-1,4-dihydro-4-oxo(1,3)dioxolo(4,5-g)cinnoline-3-carboxylate)2(H2O)2}
Conditions | Yield |
---|---|
With NaOH; H2O In dimethyl sulfoxide mixing DMSO soln. of cinoxacin and of the Ni salt, slow addn. of 5 ml of aq. NaOH with stirring, crystn. of Ni(cinoxacinate)2*2H2O after 1 d; filtration, washing (water), drying at 90°C, crystn. of the Ni complex contg. dimethyl sulfoxide ligands after 2-3 months from the remaining soln., filtration, drying at room temp., elem. anal.; | A 10% B 80% |
cinoxacin
1,2,3-Benzotriazole
3-(1H-benzo[d][1,2,3]triazole-1-carbonyl)-1-ethyl-[1,3]dioxolo[4,5-g]cinnolin-4(1H)-one
Conditions | Yield |
---|---|
Stage #1: 1,2,3-Benzotriazole With thionyl chloride In dichloromethane at 25℃; for 0.5h; Stage #2: cinoxacin In dichloromethane at 25℃; for 2h; | 80% |
Conditions | Yield |
---|---|
With NaOH; H2O In dimethyl sulfoxide mixing of a DMSO soln. of cinoxacin and of ZnCl2, addn. of 1 ml of aq. NaOH with stirring, pptn. of Zn(cinoxacinate)2*4H2O after 12-14 d; filtration, washing (water), drying at 90°C, remaining soln. standing at room temp., crystn. of the Zn complex (contg. additionally DMSO ligands) after a few d, filtration, drying at room temp., elem. anal.; | A 75% B 6% |
cinoxacin
1-ethyl-5-nitro-4-oxo-1,4-dihydro-[1,3]dioxolo[4,5-g]cinnolin-3-carboxylic acid
Conditions | Yield |
---|---|
With sulfuric acid; potassium nitrate at 0 - 20℃; for 13h; Inert atmosphere; | 75% |
cinoxacin
methanol
methyl 1-ethyl-6,7-dihydroxy-4-oxo-1,4-dihydrocinnolin-3-carboxylate
Conditions | Yield |
---|---|
Stage #1: cinoxacin With boron tribromide In dichloromethane at -30 - 20℃; for 41h; Inert atmosphere; Stage #2: methanol In dichloromethane at -30 - 20℃; Inert atmosphere; | 74.5% |
cinoxacin
A
1-Ethyl-1H-[1,3]dioxolo[4,5-g]cinnolin-4-one
Conditions | Yield |
---|---|
With oxygen In methanol for 12h; Ambient temperature; Irradiation; in PBS-solution (pH=8); Yields of byproduct given; | A n/a B 62% |
With oxygen In methanol for 12h; Mechanism; Product distribution; Ambient temperature; Irradiation; Iin PBS-solution (pH=8); | |
With oxygen In methanol for 12h; Ambient temperature; Irradiation; in PBS-solution (pH=8); Yields of byproduct given; | A 0.580 mol B n/a |
cinoxacin
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2
water
toluene
Conditions | Yield |
---|---|
With NaOCH3 In methanol; chloroform byproducts: NaCl; addn. of sodium methylate to soln. of ruthenium compd. and sodium nalidixicate in CHCl3/methanol (1/1), refluxing for 6 h; filtration through celite, addn. of toluene, keeping at room temp. with slow evapn. for 3 d, isolation of crystals, washing with hexane, elem. anal.; | 55% |
cinoxacin
1-ethyl-1,4-dihydro-4-oxo[1,3]dioxolo[4,5-g]cinnoline-3-carbonitrile
Conditions | Yield |
---|---|
Stage #1: cinoxacin With polyphosphate ester; ammonia In chloroform at 119 - 123℃; for 24h; Stage #2: With polyphosphate ester at 120℃; for 1h; | 21% |
cinoxacin
dimethyl sulfoxide
Conditions | Yield |
---|---|
With NaOH In dimethyl sulfoxide mixing DMSO solns. of cinoxacin (0.4 mmol) and CdCl2*2.5H2O (0.1 mmol); slow addn. of NaOH (0.1 M) with continuous stirring;; slow evapn. at room temp.; crystn. after 2-3 mo; elem. anal.;; | 12% |
cinoxacin
5-ethyl-5H-[1,3]dioxolo[4,5-f]indole-6,7-dione
Conditions | Yield |
---|---|
In formic acid; water (electrochemical reduction); |
cinoxacin
2-mercaptoethylamine hydrochloride
1-Ethyl-N-(2-mercaptoethyl)-6,7-methylene-dioxy-4(1H)-oxocinnoline-3-carboxamide
Conditions | Yield |
---|---|
With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide |
cinoxacin
1-Ethyl-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carboxylic acid, methyl ester
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In methanol; water |
cinoxacin
Conditions | Yield |
---|---|
With sodium hydroxide In water; dimethyl sulfoxide Co(ClO4)2*6H2O mixed with cinoxacin; soln. NaOH added with stirring for1 h; filtered; washed (DMSO); dreid in vac. at 50°C to const. wt.; elem. anal.; powd. XRD; TG-DTA; |
cinoxacin
Conditions | Yield |
---|---|
With sodium hydroxide In water; dimethyl sulfoxide cinoxacin mixed with Cu(NO3)2*3H2O; NaOH added with stirring; ppt. filtered; washed (DMSO); dried in vac. at 50°C; elem. anal.; powd. XRD, TG-DTA; |
cinoxacin
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; water cinoxacin mixed with Ni(ClO4)2*6H2O; NaOH added with stirring; evapn. at room temp. for several d; filtered; washed (methanol); dried in vac. at 50°C; elem. anal.; powd. XRD, TG-DTA; |
Conditions | Yield |
---|---|
With NaOH In ethanol; water addn. of freshly prepared soln. of histamine in ethanol to aq. soln. of copper salt, addn. of an aq. soln. of cinoxacin with NaOH; cooling overnight, filtration, cooling filtrate in refrigerator for 7- 8months; elem. anal.; |
cinoxacin
Conditions | Yield |
---|---|
In methanol stoich. amts., warm solvent; pptn. on standing for few d, collection (filtration); single crystals fro mother liquor on slow evapn.; |
Conditions | Yield |
---|---|
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide |
cinoxacin
1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-3-(pyrrolidin-1-ylmethyl)cinnolin-4(1H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: boron tribromide / dichloromethane / 41 h / -30 - 20 °C / Inert atmosphere 1.2: -30 - 20 °C / Inert atmosphere 2.1: potassium carbonate; potassium iodide / acetone / Inert atmosphere; Reflux 3.1: potassium hydroxide / methanol; water / 1.5 h / Inert atmosphere; Reflux 3.2: 20 °C / pH 1 / Inert atmosphere 4.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 4.2: 2 h / 20 °C / Inert atmosphere 5.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere 6.1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 1.5 h / 20 °C / Inert atmosphere View Scheme |
cinoxacin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: boron tribromide / dichloromethane / 41 h / -30 - 20 °C / Inert atmosphere 1.2: -30 - 20 °C / Inert atmosphere 2.1: potassium carbonate; potassium iodide / acetone / Inert atmosphere; Reflux 3.1: potassium hydroxide / methanol; water / 1.5 h / Inert atmosphere; Reflux 3.2: 20 °C / pH 1 / Inert atmosphere 4.1: thionyl chloride / dichloromethane / 1 h / Inert atmosphere; Reflux View Scheme |
cinoxacin
1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-N-(2-(pyrrolidin-1-yl)ethyl)-1,4-dihydrocinnolin-3-carboxamide
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: boron tribromide / dichloromethane / 41 h / -30 - 20 °C / Inert atmosphere 1.2: -30 - 20 °C / Inert atmosphere 2.1: potassium carbonate; potassium iodide / acetone / Inert atmosphere; Reflux 3.1: potassium hydroxide / methanol; water / 1.5 h / Inert atmosphere; Reflux 3.2: 20 °C / pH 1 / Inert atmosphere 4.1: thionyl chloride / dichloromethane / 1 h / Inert atmosphere; Reflux 5.1: triethylamine / dichloromethane / 0.5 h / 20 °C / Cooling with ice View Scheme |
cinoxacin
1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-3-(piperidin-1-ylmethyl)cinnolin-4(1H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: boron tribromide / dichloromethane / 41 h / -30 - 20 °C / Inert atmosphere 1.2: -30 - 20 °C / Inert atmosphere 2.1: potassium carbonate; potassium iodide / acetone / Inert atmosphere; Reflux 3.1: potassium hydroxide / methanol; water / 1.5 h / Inert atmosphere; Reflux 3.2: 20 °C / pH 1 / Inert atmosphere 4.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 4.2: 2 h / 20 °C / Inert atmosphere 5.1: methanesulfonyl chloride; triethylamine / dichloromethane / 2 h / Cooling with ice; Inert atmosphere 5.2: Inert atmosphere View Scheme |
cinoxacin
5-amino-1-ethyl-4-oxo-1,4-dihydro-[1,3]dioxolo[4,5-g]cinnolin-3-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sulfuric acid; potassium nitrate / 13 h / 0 - 20 °C / Inert atmosphere 2: hydrogenchloride; palladium on activated charcoal; hydrogen; acetic acid / 5 h / 2585.81 Torr / Inert atmosphere View Scheme |
cinoxacin
3-carboxy-1-ethyl-4-oxo-1,4-dihydro-[1,3]dioxolo[4,5-g]cinnolin-5-diazonium chloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sulfuric acid; potassium nitrate / 13 h / 0 - 20 °C / Inert atmosphere 2: hydrogenchloride; palladium on activated charcoal; hydrogen; acetic acid / 5 h / 2585.81 Torr / Inert atmosphere 3: hydrogenchloride; sodium nitrite / water / 5 h / 45 °C / Inert atmosphere View Scheme |
cinoxacin
5-chloro-1-ethyl-6,7-dihydroxy-4-oxo-1,4-dihydrocinnolin-3-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: sulfuric acid; potassium nitrate / 13 h / 0 - 20 °C / Inert atmosphere 2: hydrogenchloride; palladium on activated charcoal; hydrogen; acetic acid / 5 h / 2585.81 Torr / Inert atmosphere 3: hydrogenchloride; sodium nitrite / water / 5 h / 45 °C / Inert atmosphere 4: sulfuric acid / 20 h / 95 °C / Inert atmosphere View Scheme |
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