1,7-dimethyl-6,8-dioxo-3-phenyl-1,4,6,7,8-pentahydropyrimido<4,3-c>-as-triazine | 68871-22-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1,7-dimethyl-6,8-dioxo-3-phenyl-1,4,6,7,8-pentahydropyrimido<4,3-c>-as-triazine
• 英文别名: 1,7-dimethyl-3-phenyl-1,4-dihydro-pyrimido[6,1-c][1,2,4]triazine-6,8-dione；1,7-dimethyl-3-phenyl-4H-pyrimido[6,1-c][1,2,4]triazine-6,8-dione
• CAS: 68871-22-7
• 化学式: C₁₄H₁₄N₄O₂
• 分子量: 270.291
• InChiKey: FGQDAAGXNIYDNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  56.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲基-6-(1-甲基肼基)-2,4(1H,3H)-嘧啶二酮 以45%的产率得到
  参考文献：
  名称：

  YONEDA F.; HIGUCHI H.; KAWAMURA H.; NITTA Y., HETEROCYCLES, 1978, 9, NO 11, 1571-1576

  摘要：

  DOI：

文献信息

• Syntheses and properties of 4-deazatoxoflavins and related compounds.
  作者：FUMIO YONEDA、KEISHI NAKAGAWA、AKIRA KOSHIRO、TOSHIO FUJITA、YUKIKO HARIMA

  DOI：10.1248/cpb.30.172

  日期：——

  Treatment of 6-(1-methylhydrazino) uracil (I) with phenacyl bromides in methoxyethanol afforded the corresponding 3-aryl-1-methylpyrimido [4, 5-c] pyridazine-5, 7 (1H, 6H)-diones (3-aryl-6-demethyl-4-deazatoxoflavins) (II) and 3-aryl-5, 7-dioxo-1-methyl-1, 4, 5, 6, 7-pentahydropyrimido [4, 3-c] [1, 2, 4] triazines (III). Methylation of II and III with methyl iodide gave the corresponding 3-aryl-4-deazatoxoflavins (IV) and 1, 6-dimethyl-5, 7-dioxopyrimido [4, 3-c] [1, 2, 4] triazines (V). The reaction of IV with m-chloroperbenzoic acid in chloroform gave the corresponding 3-aryl-4, 4a-epoxy-4-deazatoxoflavins (VI). The oxidizing abilities of II toward alcohols were examined in comparison with those of IV from both kinetic and synthetic viewpoints. Treatment of IV with 30% aqueous caustic alkali led to the exclusive formation of 4, 8-dihydro-4-deazatoxoflavins (VII) and 4, 8-dihydro-4-deazatoxoflavin-4-ones (VIII) via intermolecular oxidation-reduction between the initially formed 4-hydroxy-4, 8-dihydro-4-deazatoxoflavins (IX) and unchanged IV. Treatment of VI with 10% aqueous sodium hydroxide gave the 6-aryl-4-hydroxy-2-methylpyridazine-3 (2H)-ones (X).

  将6-(1-甲基肼基)尿嘧啶(I)与苯乙烯溴化物在甲氧基乙醇中反应，得到相应的3-芳基-1-甲基吡啶并[4, 5-c]吡唑-5, 7(1H, 6H)-二酮（3-芳基-6-去甲基-4-去氢氧类黄素)(II)和3-芳基-5, 7-二氧基-1-甲基-1, 4, 5, 6, 7-五氢吡啶并[4, 3-c][1, 2, 4]三嗪(III)。用碘甲烷对II和III进行甲基化反应，得到相应的3-芳基-4-去氢氧类黄素(IV)和1, 6-二甲基-5, 7-二氧吡啶并[4, 3-c][1, 2, 4]三嗪(V)。IV与对氯过苯甲酸在氯仿中反应，生成相应的3-芳基-4, 4a-环氧-4-去氢氧类黄素(VI)。从动力学和合成的角度比较了II对醇的氧化能力与IV的氧化能力。IV与30%水合苛性碱反应，专一性地生成4, 8-二氢-4-去氢氧类黄素(VII)和4, 8-二氢-4-去氢氧类黄素-4-酮(VIII)，该反应通过最初形成的4-羟基-4, 8-二氢-4-去氢氧类黄素(IX)与未改变的IV之间的分子间氧化还原反应进行。VI与10%水合氢氧化钠反应，得到6-芳基-4-羟基-2-甲基吡嗪-3(2H)-酮(X)。
• Syntheses of 1,6-dimethylpyrimido(4,5-c)pyridazine-5,7(1H, 6H)-diones (4-deazatoxoflavins) and their use in the autorecycling oxidation of alcohols and amines.
  作者：FUMIO YONEDA、KEISHI NAKAGAWA、MITSUKO NOGUCHI、MASATSUGU HIGUCHI

  DOI：10.1248/cpb.29.379

  日期：——

  Treatment of 3-methyl-6-(1-methylhydrazino) uracil (I) with phenacyl bromides in ethanol afforded the corresponding 3-aryl-4, 8-dihydro-1, 6-dimethylpyrimido [4, 5-c]-pyridazine-5, 7 (1H, 6H)-diones (3-aryl-4, 8-dihydro-4-deazatoxoflavins) (II) and 3-aryl-1, 7-dimethyl-6, 8-dioxo-1, 4, 6, 7, 8-pentahydropyrimido [4, 3-c]-as-triazines (III). Oxidation of II with diethyl azodicarboxylate gave the corresponding 3-aryl-4-deazatoxoflavins (IV) in quantitative yields. The reaction of aryl aldehyde N-methyl-N-(3-methyluracil-6-yl)-hydrazones (VII) with triethyl orthoformate in dimethylformamide also gave the corresponding 3-aryl-4-deazatoxoflavins (IV). Compounds IV thus obtained oxidized alcohols under alkaline conditions in the dark to yield the corresponding carbonyl compounds, while they themselves were hydrogenated to compounds II. Under certain conditions, these oxidations were automatically recycled to give the corresponding carbonyl compounds in more than 100% yields.

  在乙醇中将 3-甲基-6-(1-甲基肼基)尿嘧啶(I)与苯乙酰溴处理，可得到相应的 3-芳基-4，8-二氢-1，6-二甲基嘧啶并[4，5-c]哒嗪-5、7(1H，6H)-二酮（3-芳基-4，8-二氢-4-脱氮恶黄素）（II）和 3-芳基-1，7-二甲基-6，8-二氧代-1，4，6，7，8-五氢嘧啶并[4，3-c]-as-三嗪（III）。用偶氮二甲酸二乙酯对 II 进行氧化，可以定量得到相应的 3-芳基-4-脱氮恶黄素（IV）。芳基醛 N-甲基-N-（3-甲基尿嘧啶-6-基）-肼（VII）与原甲酸三乙酯在二甲基甲酰胺中的反应也得到了相应的 3-芳基-4-脱氮恶黄素（IV）。这样得到的化合物 IV 在黑暗的碱性条件下氧化醇，生成相应的羰基化合物，而它们本身则氢化成化合物 II。在某些条件下，这些氧化反应会自动循环，生成相应的羰基化合物，收率超过 100%。
• YONEDA FUMIO; NAKAGAWA KEISHI; NOGUCHI MITSUKO; HIGUCHI MASATSUGU, CHEM. AND PHARM. BULL., 1981, 29, NO 2, 379-385
  作者：YONEDA FUMIO、 NAKAGAWA KEISHI、 NOGUCHI MITSUKO、 HIGUCHI MASATSUGU

  DOI：——

  日期：——
• YONEDA F.; HIGUCHI H.; KAWAMURA H.; NITTA Y., HETEROCYCLES, 1978, 9, NO 11, 1571-1576
  作者：YONEDA F.、 HIGUCHI H.、 KAWAMURA H.、 NITTA Y.

  DOI：——

  日期：——