合成路线:The title compound has also been obtained by solid phase synthesis.Bromoacetic acid (I) is coupled to hydroxymethyl polystyrene resin by means of DIC/DMAP to produce the bromoacetyl resin (II).Bromide displacement with tert-butyl carbazate (III) leads to the N-Boc hydrazino ester (IV),which is further deprotected to (V) employing trifluoroacetic acid.The hydrazinoacetic acid-bound resin (V) is then condensed with 5-(p-nitrophenyl)furfural (VI) to furnish hydrazone (VII).Acylation of resin (VII) with p-nitrophenyl chloroformate (VIII) produces the p-nitrophenyl carbamate (IX),which upon treatment with ammonia gives rise to the semicarbazone (X).Finally,concomitant intramolecular ring closure and resin cleavage of (X) produces the target aminohydantoin derivative (XI) (4,5).
参考文献标题:Solid phase synthesis of 1-aminohydantoins
文献作者:Portlock,D.E.; Li,M.; Wilson,L.J.(The Procter & Gamble Co.)
参考来源:WO 9942450
合成路线:Diazotization of 4-nitroaniline (I),followed by copper-catalyzed coupling of the resultant diazonium salt (II) with 2-furaldehyde (III) leads to 5-(p-nitrophenyl)-2-furancarboxaldehyde (IV) (1).Cyclization of semicarbazideacetic acid (V) by heating in aqueous sulfuric acid leads to 1-aminohydantoin (VI) (2).This is then condensed with aldehyde (IV) to furnish the furfurylidene aminohydantoin (VII) (1,2).Treatment of (VII) with sodium methoxide gives rise to the corresponding sodium salt (1).
参考文献标题:1-[(5-Arylfurfurylidene)amino]hydantoins.A new class of muscle relaxants
文献作者:Snyder,H.R.Jr.; Davis,C.S.; Bickerton,R.K.; Halliday,R.P.
参考来源:J Med Chem 1967,10(5),807
合成路线:Diazotization of 4-nitroaniline (I),followed by copper-catalyzed coupling of the resultant diazonium salt (II) with 2-furaldehyde (III) leads to 5-(p-nitrophenyl)-2-furancarboxaldehyde (IV) (1).Cyclization of semicarbazideacetic acid (V) by heating in aqueous sulfuric acid leads to 1-aminohydantoin (VI) (2).This is then condensed with aldehyde (IV) to furnish the furfurylidene aminohydantoin (VII) (1,2).Treatment of (VII) with sodium methoxide gives rise to the corresponding sodium salt (1).
参考文献标题:Furan derivatives.XXIII.Synthesis and absorption spectra of 5-(nitrophenyl)-2-furaldehyde derivatives
文献作者:Frimm,R.; Kovac,S.; Giller,S.A.
参考来源:Chem Zvesti 1969,23(11-12),916
合成路线:The title compound has also been obtained by solid phase synthesis.Bromoacetic acid (I) is coupled to hydroxymethyl polystyrene resin by means of DIC/DMAP to produce the bromoacetyl resin (II).Bromide displacement with tert-butyl carbazate (III) leads to the N-Boc hydrazino ester (IV),which is further deprotected to (V) employing trifluoroacetic acid.The hydrazinoacetic acid-bound resin (V) is then condensed with 5-(p-nitrophenyl)furfural (VI) to furnish hydrazone (VII).Acylation of resin (VII) with p-nitrophenyl chloroformate (VIII) produces the p-nitrophenyl carbamate (IX),which upon treatment with ammonia gives rise to the semicarbazone (X).Finally,concomitant intramolecular ring closure and resin cleavage of (X) produces the target aminohydantoin derivative (XI) (4,5).
参考文献标题:Solid phase synthesis of 1-aminohydantoin libraries
文献作者:Wilson,L.J.; Li,M.; Portlock,D.E.
参考来源:Tetrahedron Lett 1998,39(29),5135
产品链接: CAS No. 14663-23-1›› 产品链接: CAS No.7261-97-4››