3-amino-4-cyano-5-methylsulfanyl-1H-pyrrole-2-carboxylic acid ethyl ester | 124476-10-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-amino-4-cyano-5-methylsulfanyl-1H-pyrrole-2-carboxylic acid ethyl ester
• 英文别名: 3-amino-4-cyano-5-methylthio-1H-2-pyrrolecarboxylic acid ethyl ester；ethyl 3-amino-4-cyano-5-methylsulfanyl-1H-pyrrole-2-carboxylate
• CAS: 124476-10-4
• 化学式: C₉H₁₁N₃O₂S
• 分子量: 225.271
• InChiKey: QWFWLPJNARWUBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-amino-4-cyano-5-methylsulfanyl-1H-pyrrole-2-carboxylic acid ethyl ester 在 乙醇 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.5h， 生成 (7-cyano-6-methylthio-4-oxo-3,4-dihydropyrrolo[3,2-d]pyrimidin-2-ylsulfanyl)acetic acid ethyl ester
  参考文献：
  名称：

  New Syntheses of 2-Alkylthio-4-oxo-3,4-dihydroquinazolines, 2 - Alkylthio - quinazolines, as well as Their Hetero Analogues

  摘要：

  N-Chloroacetylanthranilic acid ethyl ester reacts with potassium thiocyanate in the presence of alcohol to give the (4-oxo-3,4-dihydroquinazolin-2-yl-sulfanyl)acetic acid ester (3a). In the presence of water or amines the acetic acid derivative (3b) or the acetamide derivatives (3c,d) are obtained. 2-Amino-di-oxo-3,4-dihydroquinazolines (4) arise if vigorous reaction conditions are employed. Analogously, N-chloroacetyl derivatives of 5-membered heterocycles with enaminocarbonyl structure (5, 7, 9, 11, 13, 20, 23) react with potassium thiocyanate to yield thieno[2,3-d]-, thieno[3,2-d]-, imidazo[4,5-d]-, pyrrolo[3,2-d]-, and thiazolo[4,5-d]pyrimidines (6, 8, 10, 12, 14, 21, 24). Quinazolines (18, 19) are formed from the reaction of 2-chloroacetylaminoacetophenone (16a) and 2-chloroacetylaminobenzophenone (16b) with potassium thiocyanate and subsequent treatment of the intermediates with. amines.

  DOI：

  10.3987/com-00-8954
• 作为产物：
  描述：

  N-<2,2-Dicyan-1-(methylthio)vinyl>glycin-ethylester 在 三乙胺 作用下， 反应 1.0h， 以85%的产率得到3-amino-4-cyano-5-methylsulfanyl-1H-pyrrole-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Erdmann, Barbara; Knoll, A.; Liebscher, J., Journal fur praktische Chemie (Leipzig 1954), 1988, vol. 330, # 6, p. 1015 - 1021

  摘要：

  DOI：

文献信息

• Synthesis of substituted 4-azaisoindoles — New tacrine analogues
  作者：Henri Bekolo、Gilbert Kirsch

  DOI：10.1139/v06-180

  日期：2007.1.1

  reaction of 3-amino-4-cyanopyrroles with a series of cyclic ketones has enabled the first reported synthesis of substituted 4-azaisoindoles. Structurally, this new class of compounds stands for the first reported 4-azaisoindole tacrine analogues. A reaction mechanism for the formation of the reported 4-azaisoindoles is proposed.Key words: 4-azaisoindoles, tacrine, Friedlander reaction, pyrroles, mechanism

  3-氨基-4-氰基吡咯与一系列环酮的区域选择性弗里德兰德反应使首次报道的取代4-氮杂异吲哚合成成为可能。在结构上，这一类新化合物代表了首次报道的 4-氮杂异吲哚他克林类似物。提出了形成已报道的4-氮杂异吲哚的反应机理。关键词：4-氮杂异吲哚，他克林，弗里德兰德反应，吡咯，机理。
• An Easy Access to Variously Substituted Pyrroles Starting From Ketene Dithioacetals
  作者：Geoffroy L. Sommen、Alain Comel、Gilbert Kirsch

  DOI：10.1081/scc-200050365

  日期：2005.3.1

  Abstract Variously substituted pyrroles 4 can easily be synthesized in two steps by reacting a primary or secondary amine and a ketene dithioacetal in a basic medium in moderate to good yield. Ketene dithioacetals 2 are readily prepared from acetylaceton or malononitrile, carbon disulfide, and methyl iodide.

  摘要 通过伯胺或仲胺与乙烯酮二硫缩醛在碱性介质中以中等至良好的收率反应，可以很容易地分两步合成不同取代的吡咯4。乙烯酮二硫缩醛 2 很容易从乙酰丙酮或丙二腈、二硫化碳和甲基碘制备。
• ERDMANN, BARBARA;KNOLL, A.;LIEBSCHER, J., J. PRAKT. CHEM., 330,(1988) N, C. 1015-1021
  作者：ERDMANN, BARBARA、KNOLL, A.、LIEBSCHER, J.

  DOI：——

  日期：——
• Erdmann, Barbara; Knoll, A.; Liebscher, J., Journal fur praktische Chemie (Leipzig 1954), 1988, vol. 330, # 6, p. 1015 - 1021
  作者：Erdmann, Barbara、Knoll, A.、Liebscher, J.

  DOI：——

  日期：——
• New Syntheses of 2-Alkylthio-4-oxo-3,4-dihydroquinazolines, 2 - Alkylthio - quinazolines, as well as Their Hetero Analogues
  作者：Margit Gruner、Matthias Rehwald、Katrin Eckert、Karl Gewald

  DOI：10.3987/com-00-8954

  日期：——

  N-Chloroacetylanthranilic acid ethyl ester reacts with potassium thiocyanate in the presence of alcohol to give the (4-oxo-3,4-dihydroquinazolin-2-yl-sulfanyl)acetic acid ester (3a). In the presence of water or amines the acetic acid derivative (3b) or the acetamide derivatives (3c,d) are obtained. 2-Amino-di-oxo-3,4-dihydroquinazolines (4) arise if vigorous reaction conditions are employed. Analogously, N-chloroacetyl derivatives of 5-membered heterocycles with enaminocarbonyl structure (5, 7, 9, 11, 13, 20, 23) react with potassium thiocyanate to yield thieno[2,3-d]-, thieno[3,2-d]-, imidazo[4,5-d]-, pyrrolo[3,2-d]-, and thiazolo[4,5-d]pyrimidines (6, 8, 10, 12, 14, 21, 24). Quinazolines (18, 19) are formed from the reaction of 2-chloroacetylaminoacetophenone (16a) and 2-chloroacetylaminobenzophenone (16b) with potassium thiocyanate and subsequent treatment of the intermediates with. amines.