【药物名称】Bemoradan, RWJ-22867, Orf-22867
化学结构式(Chemical Structure):
参考文献No.202017
标题:Bemoradan and related pyridazinone cardiotonics
作者:Combs, D.W.
来源:Drugs Fut 1993,18(2),139
合成路线图解说明:

The acylation of benzoxazolin-2-one (I) with propionic anhydride (II) by means of P2O5 and MsOH gives 6-propionylbenzoxazolin-2-one (III), which is treated with chloroacetyl chloride to yield 7-propionyl-3,4-dihydro-2H-1,4-benzoxazin-3-one (IV). The Mannich condensation of (IV) with CH2O and NH3 followed by methylation with methyl iodide affords the trimethylammonium compound (V), which by reaction with KCN, followed by hydrolysis with HCl gives 3-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-ylcarbonyl)butyric acid (VI). Finally this compound is cyclized with hydrazine to furnish the target pyridazinone.

参考文献No.803838
标题:Electrophilic substitutions of 2H-1,4-benzoxazine-3-one: Acylation and chlorosulfonation
作者:Kryvenko, M.; Techer, H.; Lavergne, M.; et al.
来源:CR Acad Sci Paris Ser C 1970,270(19),1601
合成路线图解说明:

The acylation of benzoxazolin-2-one (I) with propionic anhydride (II) by means of P2O5 and MsOH gives 6-propionylbenzoxazolin-2-one (III), which is treated with chloroacetyl chloride to yield 7-propionyl-3,4-dihydro-2H-1,4-benzoxazin-3-one (IV). The Mannich condensation of (IV) with CH2O and NH3 followed by methylation with methyl iodide affords the trimethylammonium compound (V), which by reaction with KCN, followed by hydrolysis with HCl gives 3-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-ylcarbonyl)butyric acid (VI). Finally this compound is cyclized with hydrazine to furnish the target pyridazinone.

参考文献No.803839
标题:6-Acyl benzoxazolinones. I
作者:Bonte, J.P.; Lesier, D.; Lespagnol, C.; et al.
来源:Eur J Med Chem - Chim Ther 1974,9491
合成路线图解说明:

The acylation of benzoxazolin-2-one (I) with propionic anhydride (II) by means of P2O5 and MsOH gives 6-propionylbenzoxazolin-2-one (III), which is treated with chloroacetyl chloride to yield 7-propionyl-3,4-dihydro-2H-1,4-benzoxazin-3-one (IV). The Mannich condensation of (IV) with CH2O and NH3 followed by methylation with methyl iodide affords the trimethylammonium compound (V), which by reaction with KCN, followed by hydrolysis with HCl gives 3-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-ylcarbonyl)butyric acid (VI). Finally this compound is cyclized with hydrazine to furnish the target pyridazinone.

参考文献No.803840
标题:6-Acyl benzoxazolinones. II. Preparation of some transformation products
作者:Lesier, D.; Lespagnol, C.; Bonte, J.P.; et al.
来源:Eur J Med Chem - Chim Ther 1974,9497-500
合成路线图解说明:

The acylation of benzoxazolin-2-one (I) with propionic anhydride (II) by means of P2O5 and MsOH gives 6-propionylbenzoxazolin-2-one (III), which is treated with chloroacetyl chloride to yield 7-propionyl-3,4-dihydro-2H-1,4-benzoxazin-3-one (IV). The Mannich condensation of (IV) with CH2O and NH3 followed by methylation with methyl iodide affords the trimethylammonium compound (V), which by reaction with KCN, followed by hydrolysis with HCl gives 3-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-ylcarbonyl)butyric acid (VI). Finally this compound is cyclized with hydrazine to furnish the target pyridazinone.

参考文献No.803841
标题:6-Aryl-4,5-dihydro-3(2H)-pyridazinones. A new class of compounds with platelet aggregation inhibiting and hypotensive activities
作者:Thyes, M.; Lehmann, H.D.; Gries, J.; et al.
来源:J Med Chem 1983,26(6),800
合成路线图解说明:

The acylation of benzoxazolin-2-one (I) with propionic anhydride (II) by means of P2O5 and MsOH gives 6-propionylbenzoxazolin-2-one (III), which is treated with chloroacetyl chloride to yield 7-propionyl-3,4-dihydro-2H-1,4-benzoxazin-3-one (IV). The Mannich condensation of (IV) with CH2O and NH3 followed by methylation with methyl iodide affords the trimethylammonium compound (V), which by reaction with KCN, followed by hydrolysis with HCl gives 3-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-ylcarbonyl)butyric acid (VI). Finally this compound is cyclized with hydrazine to furnish the target pyridazinone.

参考文献No.803842
标题:An aternative synthesis of cardiotonic 6-(3,4-dihydro-3-oxo-1,4[2H]benzoxazin-7-yl)-2,3,4,5-tetrahydro-5-methylpyridazin-3-ones
作者:Moussavi, Z.; Lesieur, D.; Depreux, P.
来源:Synth Commun 1991,21(2),271
合成路线图解说明:

The acylation of benzoxazolin-2-one (I) with propionic anhydride (II) by means of P2O5 and MsOH gives 6-propionylbenzoxazolin-2-one (III), which is treated with chloroacetyl chloride to yield 7-propionyl-3,4-dihydro-2H-1,4-benzoxazin-3-one (IV). The Mannich condensation of (IV) with CH2O and NH3 followed by methylation with methyl iodide affords the trimethylammonium compound (V), which by reaction with KCN, followed by hydrolysis with HCl gives 3-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-ylcarbonyl)butyric acid (VI). Finally this compound is cyclized with hydrazine to furnish the target pyridazinone.

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