3-amino-2-hydrazino-carbonylquinazolin-4(3H)-one | 34127-32-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-amino-2-hydrazino-carbonylquinazolin-4(3H)-one
• 英文别名: 3-amino-2-hydrazinocarbonylquinazolin-4(3H)-one；2-hydrazinocarbonyl-3-aminoquinazolin-4-one；3-amino-4-oxo-3,4-dihydro-quinazoline-2-carboxylic acid hydrazide；3-Amino-4-oxo-3,4-dihydro-chinazolin-2-carbonsaeure-hydrazid；3-Amino-2-hydrazinocarbonyl-4-chinazolon；3-Amino-4-oxoquinazoline-2-carbohydrazide
• CAS: 34127-32-7
• 化学式: C₉H₉N₅O₂
• 分子量: 219.203
• InChiKey: POPLUHJDRVYYCI-UHFFFAOYSA-N

物化性质

• 熔点：
  196-198 °C
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  16
• 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：
  114
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-amino-2-hydrazino-carbonylquinazolin-4(3H)-one 在 lead(IV) acetate 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  Reddy, V Gopal; Reddy, P S N, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 11, p. 764 - 767

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 3-(2,5-dioxopyrrolidin-1-yl)-4-oxo-3,4-dihydroquinazoline-2-carboxylate 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 以30%的产率得到3-amino-2-hydrazino-carbonylquinazolin-4(3H)-one
  参考文献：
  名称：

  Synthesis of 3-amino-3,4-dihydroquinazolin-4-one derivatives from anthranilic acid hydrazide and dicarboxylic acids

  摘要：

  Treatment of anthranilic acid hydrazide with 2 equiv of ethoxalyl chloride gave the corresponding diester which underwent cyclization in acetic anhydride to produce ethyl 3-(ethoxalylamino)-4-oxo-3,4-dihydroquinazoline-2-carboxylate. Acylation of anthranilic acid hydrazide first with succinic anhydride and then with ethoxalyl chloride led to the formation of 4-[2-(2-{[ethoxy(oxo)acetyl]amino) benzoyl)hydrazino]-4-oxobutanoic acid whose cyclization in acetic acid afforded N-(2-ethoxycarbonyl-4-oxo-3,4-dihydroquinazolin-3-yl)succinamic acid, while in acetic anhydride ethyl 3-(2,5-dioxopyrrolidin-1-yl)-4-oxo-3,4-dihydroquinazoline-2-carboxylate was obtained. The latter was brought into reactions with amines and hydrazine hydrate and alkaline hydrolysis. Acylation of 2-[2-(2-aminobenzoyl)hydrazinocarbonyl]benzoic acid with ethoxalyl chloride gave ethyl N-[2-(phthalimidocarbamoyl)phenyl]oxamate, and with succinic anhydride, 3-[4-oxo-3-phthalimido-3,4-dihydroquinazolin-2-yl]propionic acid. 4-[2-(2-Aminobenzoyl)hydrazino]-4-oxobutanoic acid reacted with phthalic anhydride in boiling acetic acid to give phthalazino[1,2-b]quinazoline-5,8-dione via elimination of succinic acid residue.

  DOI：

  10.1134/s1070428007120160

文献信息

• Reddy, P. S. N.; Reddy, V. Gopal, Synthetic Communications, 1990, vol. 20, # 1, p. 23 - 33
  作者：Reddy, P. S. N.、Reddy, V. Gopal

  DOI：——

  日期：——
• Gakhar; Sangeeta; Gupta, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 2, p. 174 - 175
  作者：Gakhar、Sangeeta、Gupta、Gupta

  DOI：——

  日期：——
• Pathak, U. S.; Rathod, I. S.; Patel, M. B., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 7, p. 617 - 623
  作者：Pathak, U. S.、Rathod, I. S.、Patel, M. B.、Shirsath, V. S.、Jain, K. S.

  DOI：——

  日期：——
• GAKHAR, H. K.;SANGEETA;GUPTA, RAMAN;GUPTA, SHASHI BHUSHAN, INDIAN J. CHEM. B , 29,(1990) N, C. 174-175
  作者：GAKHAR, H. K.、SANGEETA、GUPTA, RAMAN、GUPTA, SHASHI BHUSHAN

  DOI：——

  日期：——
• Synthesis of 3-amino-3,4-dihydroquinazolin-4-one derivatives from anthranilic acid hydrazide and dicarboxylic acids
  作者：L. A. Shemchuk、V. P. Chernykh、P. S. Arzumanov、I. L. Starchikova

  DOI：10.1134/s1070428007120160

  日期：2007.12

  Treatment of anthranilic acid hydrazide with 2 equiv of ethoxalyl chloride gave the corresponding diester which underwent cyclization in acetic anhydride to produce ethyl 3-(ethoxalylamino)-4-oxo-3,4-dihydroquinazoline-2-carboxylate. Acylation of anthranilic acid hydrazide first with succinic anhydride and then with ethoxalyl chloride led to the formation of 4-[2-(2-[ethoxy(oxo)acetyl]amino) benzoyl)hydrazino]-4-oxobutanoic acid whose cyclization in acetic acid afforded N-(2-ethoxycarbonyl-4-oxo-3,4-dihydroquinazolin-3-yl)succinamic acid, while in acetic anhydride ethyl 3-(2,5-dioxopyrrolidin-1-yl)-4-oxo-3,4-dihydroquinazoline-2-carboxylate was obtained. The latter was brought into reactions with amines and hydrazine hydrate and alkaline hydrolysis. Acylation of 2-[2-(2-aminobenzoyl)hydrazinocarbonyl]benzoic acid with ethoxalyl chloride gave ethyl N-[2-(phthalimidocarbamoyl)phenyl]oxamate, and with succinic anhydride, 3-[4-oxo-3-phthalimido-3,4-dihydroquinazolin-2-yl]propionic acid. 4-[2-(2-Aminobenzoyl)hydrazino]-4-oxobutanoic acid reacted with phthalic anhydride in boiling acetic acid to give phthalazino[1,2-b]quinazoline-5,8-dione via elimination of succinic acid residue.