合成路线:The cyclization of 3aminopyridine (I) with diethyl ethoxymethylenemalonate (II) in refluxing Dowtherm gives 4-hydroxy-1,5-naphthyridine-3-carboxylic acid ethyl ester (III),which is hydrolyzed with NaOH in refluxing water to yield the corresponding hydroxyacid (IV).The decarboxylation of (IV) by heating at 320 C in mineral oil affords 4-hydroxy-1,5-naphthyridine (V),which is acylated with trifluoromethanesulfonic anhydride to provide the triflate (VI).The reaction of (VI) with propylamine in pyridine affords 4-amino-1,5-naphthyridine (VII),which is condensed with 2-methylbenzoxazole-6-ylcarbonyl azide (VIII) (obtained by reaction of the corresponding acid (IX) with DPPA) in refluxing toluene to provide the target urea.
参考文献标题:1,3-Biarylureas as selective non-peptide antagonists of the orexin-1 receptor
文献作者:Porter,R.A.; Chan,W.N.; Coulton,S.; Johns,A.; Hadley,M.S.; Widdowson,K.; Jerman,J.C.; Brough,S.J.; Coldwell,M.C.; Smart,D.; Jewitt,F.; Jeffrey,P.; Austin,N.
参考来源:Bioorg Med Chem Lett 2001,11(14),1907
合成路线:The cyclization of 3aminopyridine (I) with diethyl ethoxymethylenemalonate (II) in refluxing Dowtherm gives 4-hydroxy-1,5-naphthyridine-3-carboxylic acid ethyl ester (III),which is hydrolyzed with NaOH in refluxing water to yield the corresponding hydroxyacid (IV).The decarboxylation of (IV) by heating at 320 C in mineral oil affords 4-hydroxy-1,5-naphthyridine (V),which is acylated with trifluoromethanesulfonic anhydride to provide the triflate (VI).The reaction of (VI) with propylamine in pyridine affords 4-amino-1,5-naphthyridine (VII),which is condensed with 2-methylbenzoxazole-6-ylcarbonyl azide (VIII) (obtained by reaction of the corresponding acid (IX) with DPPA) in refluxing toluene to provide the target urea.
参考文献标题:Synthesis of antimalarials.VI.Synthesis of certain 1,5- and 1,8-naphthyridine derivatives
文献作者:Adams,J.T.; et al.
参考来源:J Am Chem Soc 1946,681317
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