CGS-8216

2-苯基-1H-吡唑并[4,5-c]喹啉-3-酮Chemical Name: 2,5-Dihydro-2-phenyl-3H-pyrazolo[4,3-c]quinolin-3-one
CAS No. 77779-60-3
项目整合开发状态: Phase I
项目研究机构: Novartis (Originator), Pfizer (Originator)
合成路线:The condensation of aniline (I) with diethyl ethoxymethylenemalonate (II) by heating at 90 C gives diethyl anilinomethylenemalonate (III),which is cyclized to ethyl 4-hydroxyquinoline-3-carboxylate (IV) by heating at 240 C in diphenyl ether-biphenyl.The reaction of (IV) with hot POCl3 affords ethyl 4-chloro-quinoline-3-carboxylate (V),which is finally cyclized with phenylhydrazine (VI) by heating at 105 C in xylene.(VI) is prepared in the usual way starting from aniline (I) by diazotation with NaNO2-HCl to phenyldiazonium chloride (VII),and reduction with SnCl2-HCl.
📌 参考资料/链接:
参考文献标题:CGS-8216 and CGS-9896
文献作者:Serradell,M.N.; Grau,M.; Castar,J.; Blancafort,P.
参考来源:Drugs Fut 1983,8(2),99

📄 详细内容


合成路线:The condensation of aniline (I) with diethyl ethoxymethylenemalonate (II) by heating at 90 C gives diethyl anilinomethylenemalonate (III),which is cyclized to ethyl 4-hydroxyquinoline-3-carboxylate (IV) by heating at 240 C in diphenyl ether-biphenyl.The reaction of (IV) with hot POCl3 affords ethyl 4-chloro-quinoline-3-carboxylate (V),which is finally cyclized with phenylhydrazine (VI) by heating at 105 C in xylene.(VI) is prepared in the usual way starting from aniline (I) by diazotation with NaNO2-HCl to phenyldiazonium chloride (VII),and reduction with SnCl2-HCl.

合成路线:The condensation of aniline (I) with diethyl ethoxymethylenemalonate (II) by heating at 90 C gives diethyl anilinomethylenemalonate (III),which is cyclized to ethyl 4-hydroxyquinoline-3carboxylate (IV) by heating at 240 C in diphenyl ether-biphenyl.The reaction of (IV) with hot POCl3 affords ethyl-4-chloroquinoline-3-carboxylate (V),which is finally cyclized with 4-chlorophenylhydrazine (VIII) by heating at 105 C in xylene.(VIII) is prepared in the usual way starting from 4-chloroaniline (IX) by diazotation with NaNO2-HCl to 4-chlorophenyldiazonium chloride (X),and reduction with SnCl2-HCl.

参考文献标题:2-Arylpyrazolo[4,3-c]quinolin-3-ones: A partial novel agonist and antagonist of benzodiazepines
文献作者:Yokoyama,N.; Ritter,B.; Neubert,A.D.
参考来源:J Med Chem 1982,25(4),337-339


合成路线:The condensation of aniline (I) with diethyl ethoxymethylenemalonate (II) by heating at 90 C gives diethyl anilinomethylenemalonate (III),which is cyclized to ethyl 4-hydroxyquinoline-3-carboxylate (IV) by heating at 240 C in diphenyl ether-biphenyl.The reaction of (IV) with hot POCl3 affords ethyl 4-chloro-quinoline-3-carboxylate (V),which is finally cyclized with phenylhydrazine (VI) by heating at 105 C in xylene.(VI) is prepared in the usual way starting from aniline (I) by diazotation with NaNO2-HCl to phenyldiazonium chloride (VII),and reduction with SnCl2-HCl.

合成路线:The condensation of aniline (I) with diethyl ethoxymethylenemalonate (II) by heating at 90 C gives diethyl anilinomethylenemalonate (III),which is cyclized to ethyl 4-hydroxyquinoline-3carboxylate (IV) by heating at 240 C in diphenyl ether-biphenyl.The reaction of (IV) with hot POCl3 affords ethyl-4-chloroquinoline-3-carboxylate (V),which is finally cyclized with 4-chlorophenylhydrazine (VIII) by heating at 105 C in xylene.(VIII) is prepared in the usual way starting from 4-chloroaniline (IX) by diazotation with NaNO2-HCl to 4-chlorophenyldiazonium chloride (X),and reduction with SnCl2-HCl.

参考文献标题:
文献作者:Yokoyama,N.
参考来源:US 4312870


合成路线:The condensation of aniline (I) with diethyl ethoxymethylenemalonate (II) by heating at 90 C gives diethyl anilinomethylenemalonate (III),which is cyclized to ethyl 4-hydroxyquinoline-3-carboxylate (IV) by heating at 240 C in diphenyl ether-biphenyl.The reaction of (IV) with hot POCl3 affords ethyl 4-chloro-quinoline-3-carboxylate (V),which is finally cyclized with phenylhydrazine (VI) by heating at 105 C in xylene.(VI) is prepared in the usual way starting from aniline (I) by diazotation with NaNO2-HCl to phenyldiazonium chloride (VII),and reduction with SnCl2-HCl.

合成路线:The condensation of aniline (I) with diethyl ethoxymethylenemalonate (II) by heating at 90 C gives diethyl anilinomethylenemalonate (III),which is cyclized to ethyl 4-hydroxyquinoline-3carboxylate (IV) by heating at 240 C in diphenyl ether-biphenyl.The reaction of (IV) with hot POCl3 affords ethyl-4-chloroquinoline-3-carboxylate (V),which is finally cyclized with 4-chlorophenylhydrazine (VIII) by heating at 105 C in xylene.(VIII) is prepared in the usual way starting from 4-chloroaniline (IX) by diazotation with NaNO2-HCl to 4-chlorophenyldiazonium chloride (X),and reduction with SnCl2-HCl.
参考文献标题:
文献作者:Yokoyama,N.
参考来源:EP 0022078


产品链接: CAS No. 77779-60-3››