合成路线:The reaction of 2-benzoylbenzoic acid (I) with SOCl2 in CHCl3,benzene or DMF gives the corresponding acyl chloride (II),which is condensed with ethanolamine (III) by means of TEA in CHCl3 to yield the amide (IV).The reduction of (IV) with LiAlH4 in THF affords the diol (V),which is cyclized by means of Ts-OH in refluxing benzene to provide 1-phenyl-3,4,5,6-tetrahydro-1H-2,5-benzoxazocine (VI).Finally,this compound is methylated by means of dimethyl sulfate in refluxing benzene,or by means of formaldehyde in hot dioxane/water.Alternatively,the cyclization of N-[2-[1-[2-(chloromethyl)phenyl]-1-phenylmethoxy]ethyl]-N-methylamine (VII) by means of pyridine in refluxing acetonitrile gives also the target benzoxazocine.
参考文献标题:Process for the preparation of of a heterocyclic tertiary amine
文献作者:Colls Alsius,J.
参考来源:ES 8607261
合成路线:The reaction of 2-benzoylbenzoic acid (I) with SOCl2 in CHCl3,benzene or DMF gives the corresponding acyl chloride (II),which is condensed with ethanolamine (III) by means of TEA in CHCl3 to yield the amide (IV).The reduction of (IV) with LiAlH4 in THF affords the diol (V),which is cyclized by means of Ts-OH in refluxing benzene to provide 1-phenyl-3,4,5,6-tetrahydro-1H-2,5-benzoxazocine (VI).Finally,this compound is methylated by means of dimethyl sulfate in refluxing benzene,or by means of formaldehyde in hot dioxane/water.Alternatively,the cyclization of N-[2-[1-[2-(chloromethyl)phenyl]-1-phenylmethoxy]ethyl]-N-methylamine (VII) by means of pyridine in refluxing acetonitrile gives also the target benzoxazocine.
参考文献标题:Process for the preparation of diphenylcarbinol derivs.
文献作者:L醶aro Porta,A.
参考来源:ES 8100663
合成路线:The reaction of 3-phenylphthalide (I) with N-methylethanolamine (II) in refluxing benzene gives N-(2-hydroxyethyl)-2-(1-hydroxy-1-phenylmethyl)-N-methylbenzamide (III),which is cyclized by means of Ts-OH in refluxing toluene to yield 5-methyl-1-phenyl-3,4,5,6-tetrahydro-1H-2,5-benzoxazocin-6-one (IV).Finally this compound is reduced with LiAlH4 in refluxing THF to afford the target benzoxazocine.In an alternative method,the reduction of 2-benzoyl-N-(2-hydroxyethyl)-N-methylbenzamide (V) by means of sodium bis(2-methoxyethoxy)aluminum hydride in refluxing toluene gives the diol (VI),which is then cyclized by means of Ts-OH in refluxing toluene,or by means of aq.48% HBr in hot chloroform to afford the target benzoxazocine.
参考文献标题:Process for the preparation of benzoxazines
文献作者:Gimbert Roura,J.; Soler Peix,E.
参考来源:KE 8201564
合成路线:The reaction of 3-phenylphthalide (I) with N-methylethanolamine (II) in refluxing benzene gives N-(2-hydroxyethyl)-2-(1-hydroxy-1-phenylmethyl)-N-methylbenzamide (III),which is cyclized by means of Ts-OH in refluxing toluene to yield 5-methyl-1-phenyl-3,4,5,6-tetrahydro-1H-2,5-benzoxazocin-6-one (IV).Finally this compound is reduced with LiAlH4 in refluxing THF to afford the target benzoxazocine.In an alternative method,the reduction of 2-benzoyl-N-(2-hydroxyethyl)-N-methylbenzamide (V) by means of sodium bis(2-methoxyethoxy)aluminum hydride in refluxing toluene gives the diol (VI),which is then cyclized by means of Ts-OH in refluxing toluene,or by means of aq.48% HBr in hot chloroform to afford the target benzoxazocine.
参考文献标题:Process for the preparation of a benzoxazine deriv.and its non-toxic salt
文献作者:Lucero de Pablo,M.L.; Martin-Escudero Perez,U.; Izquierdo Sanjose,M.
参考来源:ES 8105723
合成路线:The reaction of 3-phenylphthalide (I) with N-methylethanolamine (II) in refluxing benzene gives N-(2-hydroxyethyl)-2-(1-hydroxy-1-phenylmethyl)-N-methylbenzamide (III),which is cyclized by means of Ts-OH in refluxing toluene to yield 5-methyl-1-phenyl-3,4,5,6-tetrahydro-1H-2,5-benzoxazocin-6-one (IV).Finally this compound is reduced with LiAlH4 in refluxing THF to afford the target benzoxazocine.In an alternative method,the reduction of 2-benzoyl-N-(2-hydroxyethyl)-N-methylbenzamide (V) by means of sodium bis(2-methoxyethoxy)aluminum hydride in refluxing toluene gives the diol (VI),which is then cyclized by means of Ts-OH in refluxing toluene,or by means of aq.48% HBr in hot chloroform to afford the target benzoxazocine.
参考文献标题:Process for benz[f]-2,5-oxazocines
文献作者:Eberlin,J.W.
参考来源:US 3978085
合成路线:The reaction of 2-benzoylbenzoic acid (I) with refluxing SOCl2 gives the corresponding acyl chloride (II),which is condensed with 2-(methylamino)acetic acid (III) in benzene to yield the N-(2-benzoylbenzoyl)-N-methylglycine (IV).The reduction of (IV) by means of LiAlH4 in refluxing THF affords the diol (V),which is finally cyclized by means of PPA at 80 C to provide the target benzoxazocine.
参考文献标题:Process for the preparation of 1-methyl-5-phenyl-aza-4-oxo-6,7-benzocyclooctane
文献作者:Galiano Ramos,J.A.; Verde Casanova,M.J.; Fernandez Torija,C.(Instituto de Investigaci髇 y Desarrollo Qu韒ico Biol骻ico SA)
参考来源:ES 8104800
产品链接: CAS No. 23327-57-3›› 产品链接: CAS No.13669-70-0››