合成路线:1) The acylation of N-(2-amino-5-nitrobenzoyl)-o-toluidine (I) with fluoroacetyl chloride by means of pyridine in THF gives N-(2-fluoroacetamido-5-nitrobenzoyl)-o-toluidine (II),which is cyclized by means of refluxing acetic anhydride acetic acid to yield 6-nitro-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone (III).Finally,this compound is reduced with H2 over Pd/C in acetic acid or with SnCl2 - HCl in methanol - water.2) The acylation of (I) with chloroacetyl chloride as before gives N-(2-chloroacetamido-5-nitro-benzoyl)-o-toluidine (IV),which is cyclized with acetic anhydride as before affording 6-nitro-2-chloromethyl-3-(o-tolyl)-4(3H)-quinazolinone (V).Finally,the treatment of (V) with KF in refluxing diethylene glycol yields (III).
合成路线:3) The reduction of (V) with SnCl2 as before gives 6-amino-2-chloromethyl-3-(o-tolyl)-4(3H)-quinazolinone (VI),which is acylated with acetyl chloride as before to yield 6-acetamido-2-chloromethyl-3-(o-tolyl)-4(3H)-quinazolinone (VII).The treatment of (VII) with KF in diethylene glycol at 160 C yields 6-acetamido-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone (VIII),which is finally deprotected by treatment with HCl in methanol.
参考文献标题:Afloqualone
文献作者:Castar,J.; Blancafort,P.; Serradell,M.N.; Sweetman,A.J.
参考来源:Drugs Fut 1982,7(8),539
合成路线:1) The acylation of N-(2-amino-5-nitrobenzoyl)-o-toluidine (I) with fluoroacetyl chloride by means of pyridine in THF gives N-(2-fluoroacetamido-5-nitrobenzoyl)-o-toluidine (II),which is cyclized by means of refluxing acetic anhydride acetic acid to yield 6-nitro-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone (III).Finally,this compound is reduced with H2 over Pd/C in acetic acid or with SnCl2 - HCl in methanol - water.2) The acylation of (I) with chloroacetyl chloride as before gives N-(2-chloroacetamido-5-nitro-benzoyl)-o-toluidine (IV),which is cyclized with acetic anhydride as before affording 6-nitro-2-chloromethyl-3-(o-tolyl)-4(3H)-quinazolinone (V).Finally,the treatment of (V) with KF in refluxing diethylene glycol yields (III).
参考文献标题:
文献作者:Inoue,I.; Oine,T.; Yamada,Y.; Tani,J.
参考来源:JP 76105083
合成路线:3) The reduction of (V) with SnCl2 as before gives 6-amino-2-chloromethyl-3-(o-tolyl)-4(3H)-quinazolinone (VI),which is acylated with acetyl chloride as before to yield 6-acetamido-2-chloromethyl-3-(o-tolyl)-4(3H)-quinazolinone (VII).The treatment of (VII) with KF in diethylene glycol at 160 C yields 6-acetamido-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone (VIII),which is finally deprotected by treatment with HCl in methanol.
参考文献标题:
文献作者:Inoue,I.; Oine,T.; Yamada,Y.; Tani,J.
参考来源:JP 76105082
产品链接: CAS No. 56287-74-2›› 产品链接: CAS No.56287-75-3››