合成路线:The reaction of 9-chlorocarbonylmethyl-9,10-dihydro-9,10-ethanoanthracene (I) with the aldehyde (II) with trimethyloxosulfonium iodide by means of NaH in DMSO gives 9-(2-epoxypropyl)-9,10-dihydro-9,10-ethanoanthracene (IX),which is then treated with methylamine in refluxing ethanol.
合成路线:The reduction of from 9-chlorocarbonylmethyl-9,10-dihydro-9,10-ethanoanthracene (I) with H2 over Pd/C poisoned with quinoline - sulfur in xylene gives 9,10-dihydro-9,10-ethano-9-anthrylacetaldehyde (II),which is condensed with HCN by means of triethylamine in methylene chloride yielding 9-(2-cyano-2-hydroxyethyl)-9,10-dihydro-9,10-ethanoanthracene (III).The reduction of (III) with LiAlH4 in refluxing THF affords 9-(2-hydroxy-3-aminopropyl)-9,10-dihydro-9,10-ethanoanthracene (IV),which is cyclized with formaldehyde in formic acid at 90 C to give 9-[(3-methyl-5-oxazolidinyl)methyl]-9,10-dihydro-9,10-ethanoanthracene (V).Finally,this compound is hydrolyzed with hot hydrochloric acid.The cyclization of the amine (IV) with phosgene by means of NaOH in dioxane-toluene gives 5-(9,10-hydro-9,10-ethano-9-anthrylmethyl)oxazolidin-2-one (VI),which is reduced with LiAlH4 in refluxing THF.
合成路线:Tosylation of the amine (IV) with tosyl chloride in pyridine gives N-(p-toluenesulfonyl)-9-(2-hydroxy-3-aminopropyl)-9,10-dihydro-9,10-ethanoanthracene (VII),which is methylated with diazomethane in ether yielding the corresponding N-methyl derivative (VIII).Finally,this compound is detosylated by treating with LiAlH4 in refluxing THF.
参考文献标题:Amines and processes for their manufacture
文献作者:Wilhelm,M.; et al.
参考来源:DE 2207097; ES 400022; FR 2126353; GB 1378241
合成路线:The reduction of from 9-chlorocarbonylmethyl-9,10-dihydro-9,10-ethanoanthracene (I) with H2 over Pd/C poisoned with quinoline - sulfur in xylene gives 9,10-dihydro-9,10-ethano-9-anthrylacetaldehyde (II),which is condensed with HCN by means of triethylamine in methylene chloride yielding 9-(2-cyano-2-hydroxyethyl)-9,10-dihydro-9,10-ethanoanthracene (III).The reduction of (III) with LiAlH4 in refluxing THF affords 9-(2-hydroxy-3-aminopropyl)-9,10-dihydro-9,10-ethanoanthracene (IV),which is cyclized with formaldehyde in formic acid at 90 C to give 9-[(3-methyl-5-oxazolidinyl)methyl]-9,10-dihydro-9,10-ethanoanthracene (V).Finally,this compound is hydrolyzed with hot hydrochloric acid.The cyclization of the amine (IV) with phosgene by means of NaOH in dioxane-toluene gives 5-(9,10-hydro-9,10-ethano-9-anthrylmethyl)oxazolidin-2-one (VI),which is reduced with LiAlH4 in refluxing THF.
参考文献标题:Verfahren zur Herstellung neuer 9-(2-Hydroxy3-Aminopropyl-9,10-dihydro-9,10-鋘thanoanthracene
文献作者:Wilhelm,M.; et al.
参考来源:CH 566293
合成路线:The reduction of from 9-chlorocarbonylmethyl-9,10-dihydro-9,10-ethanoanthracene (I) with H2 over Pd/C poisoned with quinoline - sulfur in xylene gives 9,10-dihydro-9,10-ethano-9-anthrylacetaldehyde (II),which is condensed with HCN by means of triethylamine in methylene chloride yielding 9-(2-cyano-2-hydroxyethyl)-9,10-dihydro-9,10-ethanoanthracene (III).The reduction of (III) with LiAlH4 in refluxing THF affords 9-(2-hydroxy-3-aminopropyl)-9,10-dihydro-9,10-ethanoanthracene (IV),which is cyclized with formaldehyde in formic acid at 90 C to give 9-[(3-methyl-5-oxazolidinyl)methyl]-9,10-dihydro-9,10-ethanoanthracene (V).Finally,this compound is hydrolyzed with hot hydrochloric acid.The cyclization of the amine (IV) with phosgene by means of NaOH in dioxane-toluene gives 5-(9,10-hydro-9,10-ethano-9-anthrylmethyl)oxazolidin-2-one (VI),which is reduced with LiAlH4 in refluxing THF.
合成路线:By autoclaving ethylene with 9-(2-hydroxy-3-methylaminopropyl)anthracene (X).
参考文献标题:Verfahren zur Herstellung neuer 9-(2-Hydroxy3-Aminopropyl-9,10-dihydro-9,10-鋘thanoanthracene
文献作者:Wilhelm,M.; et al.
参考来源:CH 558774
合成路线:The reduction of from 9-chlorocarbonylmethyl-9,10-dihydro-9,10-ethanoanthracene (I) with H2 over Pd/C poisoned with quinoline - sulfur in xylene gives 9,10-dihydro-9,10-ethano-9-anthrylacetaldehyde (II),which is condensed with HCN by means of triethylamine in methylene chloride yielding 9-(2-cyano-2-hydroxyethyl)-9,10-dihydro-9,10-ethanoanthracene (III).The reduction of (III) with LiAlH4 in refluxing THF affords 9-(2-hydroxy-3-aminopropyl)-9,10-dihydro-9,10-ethanoanthracene (IV),which is cyclized with formaldehyde in formic acid at 90 C to give 9-[(3-methyl-5-oxazolidinyl)methyl]-9,10-dihydro-9,10-ethanoanthracene (V).Finally,this compound is hydrolyzed with hot hydrochloric acid.The cyclization of the amine (IV) with phosgene by means of NaOH in dioxane-toluene gives 5-(9,10-hydro-9,10-ethano-9-anthrylmethyl)oxazolidin-2-one (VI),which is reduced with LiAlH4 in refluxing THF.
合成路线:Tosylation of the amine (IV) with tosyl chloride in pyridine gives N-(p-toluenesulfonyl)-9-(2-hydroxy-3-aminopropyl)-9,10-dihydro-9,10-ethanoanthracene (VII),which is methylated with diazomethane in ether yielding the corresponding N-methyl derivative (VIII).Finally,this compound is detosylated by treating with LiAlH4 in refluxing THF.
参考文献标题:Verfahren zur Herstellung neuer 9-(2-Hydroxy3-Aminopropyl-9,10-dihydro-9,10-鋘thanoanthracene
文献作者:Wilhelm,M.; et al.
参考来源:CH 563960
产品链接: CAS No. 39022-39-4›› 产品链接: CAS No.56433-44-4››