4-amino-6-(4-pyridinyl)-3(2H)-pyridazinone | 80843-53-4

• 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: 4-amino-6-(4-pyridinyl)-3(2H)-pyridazinone
• 英文别名: 5-amino-3-pyridin-4-yl-1H-pyridazin-6-one
• CAS: 80843-53-4
• 化学式: C₉H₈N₄O
• 分子量: 188.189
• InChiKey: GPVUOJQVQCQENB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  diethyl hydroxy<2-oxo-2-(4-pyridinyl)ethyl>propanedioate 在 盐酸 、 盐酸肼 、 一水合肼 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 26.75h， 生成 4-amino-6-(4-pyridinyl)-3(2H)-pyridazinone
  参考文献：
  名称：

  Synthesis of Aza Analogs of Amrinone

  摘要：

  The aldol condensation product (4) of 4-acetylpyridine (2) and diethyl mesoxalate (3) was converted to pyridazinecarboxylic acid hydrazide (6). Curtius reaction of 6 gave aminopyridazinone (7). The condensation of (4-pyridinyl)glyoxal (17) with aminomalonamide (9) yielded pyrazinecarboxamide (18) which was transformed to aminopyrazinone (19) by the Hofmann reaction. Curtius reaction of 1,2,4-triazinone-5-carboxylic acid (21b) gave aminotriazinone (22). Demethylation of methoxypyrimidine (29) prepared from methyl 2-methoxyformylacetate (25) and isonicotinamidine (26) gave pyrimidinol (30).

  DOI：

  10.3987/com-90-5562

文献信息

• 4-Substituted-6-(pyridinyl)-3(2h)-pyridazinones and their use as
  申请人：Sterling Drug Inc.

  公开号：US04304776A1

  公开（公告）日：1981-12-08

  2-R-4-R'-6-PY-3(2H)-pyridazinones (I) or salts thereof, which are useful as intermediates and some as cardiotonics, are prepared by reacting di-(lower-alkyl) hydroxy[2-oxo-2-PY-ethyl]propanedioate (II) with a hydrazine salt of the formula RNHNH.sub.2.nH.sub.x An (III) to produce lower-alkyl 2,3-dihydro-2-R-3-oxo-6-PY-4-pyridazinecarboxylate (Ia where R' is lower-carbalkoxy) and reacting Ia with hydrazine hydrate or anhydrous hydrazine to produce 2,3-dihydro-2-R-3-oxo-6-PY-4-pyridazinecarboxylic acid hydrazide (Ib where R' is aminocarbamyl), where PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, R is hydrogen, lower-alkyl or lower-hydroxyalkyl, R' is carbamyl, carboxy, aminocarbamyl or lower-carbalkoxy, n is 1 or 2, x is 1, 2 or 3, and An is an anion of a strong inorganic acid or an organic sulfonic acid. Also shown are: the preparation of II from PY--COCH.sub.3 (IV), the conversion of Ia to Ib (Id where R' is carboxy), and the use of 2-R-4-R"-6-PY-3(2H)-pyridazinones (I where R is lower-alkyl or lower-hydroxyalkyl and R" is carbamyl, aminocarbamyl or lower-carbalkoxy) as cardiotonic agents. Other intermediates are shown.

  2-R-4-R'-6-PY-3(2H)-吡啶嗪酮（I）或其盐，可用作中间体和一些心脏强心剂，通过将二（低烷基）羟基[2-氧代-2-PY-乙基]丙二酸酯（II）与式为RNHNH.sub.2.nH.sub.x An（III）的肼盐反应制备而成，以产生低烷基2,3-二氢-2-R-3-氧代-6-PY-4-吡啶嗪羧酸酯（其中R'为低碳基烷氧基），并将Ia与肼水合物或无水肼反应以产生2,3-二氢-2-R-3-氧代-6-PY-4-吡啶嗪羧酸肼（其中R'为氨基羰基），其中PY为4-或3-吡啶基或4-或3-吡啶基具有一个或两个低烷基取代基，R为氢、低烷基或低羟基烷基，R'为羰基、羧基、氨基羰基或低碳基烷氧基，n为1或2，x为1、2或3，An为强无机酸或有机磺酸的阴离子。还显示了从PY-COCH.sub.3（IV）制备II，将Ia转化为Ib（其中R'为羧基）以及将2-R-4-R"-6-PY-3（2H）-吡啶嗪酮（其中R为低烷基或低羟基烷基，R"为羰基、氨基羰基或低碳基烷氧基）用作心脏强心剂的用途。还显示了其他中间体。
• 4-Amino-6-(pyridinyl)-3(2H)-pyridazinones and their use as cardiotonics
  申请人：Sterling Drug Inc.

  公开号：US04305943A1

  公开（公告）日：1981-12-15

  4-Amino-2-R-6-PY-3(2H)-pyridazinones (I) or salts thereof, which are useful as cardiotonics, where R is hydrogen, lower-alkyl or lower-hydroxyalkyl, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents are prepared by: (a) reaction of 2-R-6-PY-3(2H)-pyridazinone (II) with hydrazine; (b) conversion from 2,3-dihydro-2-R-3-oxo-6-PY-4-pyridazinecarboxamide (III); or, (c) conversion form 2,3-dihydro-2-R-3-oxo-6-PY-4-pyridazinecarboxylic acid hydrazide (IV). Also shown are: the use of I or salts as cardiotonic agents; and, the preparation of intermediates.

  4-氨基-2-R-6-PY-3（2H）-吡啶嗪酮（I）或其盐，可用作心脏强心剂，其中R为氢，低烷基或低羟基烷基，PY为4-或3-吡啶基或带有一或两个低烷基取代基的4-或3-吡啶基，通过以下方法制备：（a）2-R-6-PY-3（2H）-吡啶嗪酮（II）与肼反应；（b）从2,3-二氢-2-R-3-氧代-6-PY-4-吡啶嗪羧酰胺（III）转化而来；或（c）从2,3-二氢-2-R-3-氧代-6-PY-4-吡啶嗪羧酸肼（IV）转化而来。还显示了：将I或其盐用作心脏强心剂的用途；以及中间体的制备。
• Di-(lower-alkyl)hydroxy-[2-oxo-2-(pyridinyl)ethyl]-propanedioates
  申请人：Sterling Drug Inc.

  公开号：US04338446A1

  公开（公告）日：1982-07-06

  2-R-4-R'-6-PY-3(2H)-pyridazinones (I) or salts thereof, which are useful as intermediates and some as cardiotonics, are prepared by reacting di-(lower-alkyl) hydroxy[2-oxo-2-PY-ethyl]propanedioate (II) with a hydrazine salt of the formula RNHNH.sub.2.nH.sub.x An (III) to produce lower-alkyl 2,3-dihydro-2-R-3-oxo-6-PY-4-pyridazinecarboxylate (Ia where R' is lower-carbalkoxy) and reacting Ia with hydrazine hydrate or anhydrous hydrazine to produce 2,3-dihydro-2-R-3-oxo-6-PY-4-pyridazinecarboxylic acid hydrazide (Ib where R' is aminocarbamyl), where PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, R is hydrogen, lower-alkyl or lower-hydroxyalkyl, R' is carbamyl, carboxy, aminocarbamyl or lower-carbalkoxy, n is 1 or 2, x is 1, 2 or 3, and An is an anion of a strong inorganic acid or an organic sulfonic acid. Also shown are: the preparation of II from PY-COCH.sub.3 (IV), the conversion of Ia to Ib (Id where R' is carboxy), and the use of 2-R-4-R"-6-PY-3(2H)-pyridazinones (I where R is lower-alkyl or lower-hydroxyalkyl and R" is carbamyl, aminocarbamyl or lower-carbalkoxy) as cardiotonic agents. Other intermediates are shown.

  2-R-4-R'-6-PY-3(2H)-吡嗪酮(I)或其盐，可用作中间体和一些心脏强心剂，通过将二（低烷基）羟基[2-氧代-2-PY-乙基]丙二酸酯(II)与公式RNHNH.sub.2.nH.sub.x An(III)的肼盐反应制备，以产生低烷基2,3-二氢-2-R-3-氧代-6-PY-4-吡啶嗪羧酸酯(Ia，其中R'是低碳基氧)并将Ia与肼水合物或无水肼反应，以产生2,3-二氢-2-R-3-氧代-6-PY-4-吡啶嗪羧酸肼(Ib，其中R'是氨基氨甲酰基)，其中PY是4-或3-吡啶基或4-或3-吡啶基具有一个或两个低烷基取代基，R是氢，低烷基或低羟基烷基，R'是氨甲酰基，羧基，氨基氨甲酰基或低碳基氧，n为1或2，x为1,2或3，An为强无机酸或有机磺酸的阴离子。还显示了：从PY-COCH.sub.3(IV)制备II，将Ia转化为Ib(Id，其中R'是羧基)，以及将2-R-4-R"-6-PY-3(2H)-吡嗪酮(I，其中R是低烷基或低羟基烷基，R"是氨甲酰基，氨基氨甲酰基或低碳基氧)用作心脏强心剂的用途。还显示了其他中间体。
• Preparation of 4-amino-6-(pyridinyl)-3(2H)-pyridazinones from
  申请人：Sterling Drug Inc.

  公开号：US04346221A1

  公开（公告）日：1982-08-24

  4-Amino-2-R-6-PY-3(2H)-pyridazinones (I) or salts thereof, which are useful as cardiotonics, where R is hydrogen, lower-alkyl or lower-hydroxyalkyl, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents are prepared by: (a) reaction of 2-R-6-PY-3(2H)-pyridazinone (II) with hydrazine; (b) conversion from 2,3-dihydro-2-R-3-oxo-6-PY-4-pyridazinecarboxamide (III); or, (c) conversion form 2,3-dihydro-2-R-3-oxo-6-PY-4-pyridazinecarboxylic acid hydrazide (IV). Also shown are: the use of I or salts as cardiotonic agents; and, the preparation of intermediates.

  4-氨基-2-R-6-PY-3（2H）-吡啶嗪酮（I）或其盐，可用作心脏强心剂，其中R为氢，低烷基或低羟基烷基，PY为4-或3-吡啶基或带有一个或两个低烷基取代基的4-或3-吡啶基，通过以下方法制备：（a）2-R-6-PY-3（2H）-吡啶嗪酮（II）与肼反应；（b）由2,3-二氢-2-R-3-氧代-6-PY-4-吡啶嗪羧酰胺（III）转化而来；或（c）由2,3-二氢-2-R-3-氧代-6-PY-4-吡啶嗪羧酸肼（IV）转化而来。还显示了：将I或其盐用作心脏强心剂的用途；以及中间体的制备。
• Singh, Baldev, Heterocycles, 1984, vol. 22, # 8, p. 1801 - 1804
  作者：Singh, Baldev

  DOI：——

  日期：——