methyl 6'-amino-5'-cyano-1-methyl-2-oxo-2'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-3'-carboxylate | 1454646-34-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl 6'-amino-5'-cyano-1-methyl-2-oxo-2'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-3'-carboxylate
• 英文别名: methyl 6′-amino-5′-cyano-1-methyl-2-oxo-2′H-spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-3′-carboxylate；methyl 6-amino-5-cyano-1'-methyl-2'-oxospiro[2H-pyrano[2,3-c]pyrazole-4,3'-indole]-3-carboxylate
• CAS: 1454646-34-4
• 化学式: C₁₇H₁₃N₅O₄
• 分子量: 351.321
• InChiKey: OFTTWEAPRMULCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  丁炔二酸二甲酯 在 一水合肼 、 sodium chloride 作用下， 以 水 为溶剂， 反应 0.34h， 生成 methyl 6'-amino-5'-cyano-1-methyl-2-oxo-2'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-3'-carboxylate
  参考文献：
  名称：

  Convenient NaCl-Catalysed Multicomponent Synthesis of Spiro[indoline-3,4′-Pyrano[2,3-c]Pyrazole]-3′-Carboxylate Derivatives in Aqueous Medium

  摘要：

  以氯化钠为催化剂，在水中合成了一系列 6′-氨基-5′-氰基-2-氧代-1′H-螺[吲哚啉-3,4′-吡喃并[2,3-c]吡唑]-3′-羧酸烷基酯。该绿色合成方法具有极具吸引力的绿色特点，例如以水作为反应介质、反应时间极短、易于操作以及减少废物。

  DOI：

  10.3184/174751915x14380980941797

文献信息

• A novel one pot four-component reaction for the efficient synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-3′-carboxylate and trifluoromethylated spiro[indole-3,4′-pyrano[2,3-c]pyrazole] derivatives using recyclable PEG-400
  作者：K. Karnakar、K. Ramesh、K. Harsha Vardhan Reddy、B. S. P. Anil Kumar、Jagadeesh Babu Nanubonula、Y. V. D. Nageswar

  DOI：10.1039/c5nj01448d

  日期：——

  efficient synthetic protocol has been developed for the synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-3′-carboxylate and trifluoromethylated spiro[indole-3,4′-pyrano[2,3-c]pyrazole] derivatives via a one pot, four-component reaction using recyclable polyethylene glycol (PEG-400). This new protocol produces novel spiro pyranopyrazole derivatives in good to excellent yields, with operational

  已开发出一种新颖，简单，有效的合成方案，用于合成螺[吲哚啉-3,4'-吡喃并[2,3- c ]吡唑] -3'-羧酸盐和三氟甲基化螺[吲哚-3,4'-通过使用可回收的聚乙二醇（PEG-400）进行一锅四组分反应，生成吡喃并[2,3- c ]吡唑]衍生物。该新方案以良好的产率和优异的产率生产新颖的螺并吡喃并吡唑衍生物，且操作简便且可回收PEG-400。该方法的显着特点是高收率，简便的后处理工艺以及避免有毒催化剂和有害溶剂的绿色方法。
• One pot four-component reaction for the efficient synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-3′-carboxylate derivatives
  作者：Suman Pal、Md. Nasim Khan、Shaik Karamthulla、Sk Jahir Abbas、Lokman H. Choudhury

  DOI：10.1016/j.tetlet.2013.07.117

  日期：2013.10

  to synthesize various spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-3′-carboxylate derivatives from the four-component reaction of isatin, malononitrile, hydrazine derivatives and dialkyl acetylenedicarboxylates. In this process two C–C bonds, two C–N bonds and one C–O bond have formed in one pot. The notable features of this protocol are simple and environmentally benign reaction condition, easy isolation

  已经开发了一种新颖的一锅法，该方法可以从靛红，丙二腈，肼衍生物和四价胺的四组分反应合成各种螺[吲哚啉-3,4'-吡喃并[2,3- c ]吡唑] -3'-羧酸酯衍生物。乙炔二羧酸二烷基酯。在此过程中，在一个罐中形成了两个C–C键，两个C–N键和一个C–O键。该方案的显着特征是简单且对环境无害的反应条件，易于分离的产物，适用于各种现成的起始原料和良好的收率。
• Green access to novel spiro pyranopyrazole derivatives
  作者：D.M. Pore、P.B. Patil、D.S. Gaikwad、P.G. Hegade、J.D. Patil、K.A. Undale

  DOI：10.1016/j.tetlet.2013.08.084

  日期：2013.10

  A catalyst-free multicomponent reaction (MCR) capable of affording a wide range of novel spiro pyranopyrazole derivatives from pyrazolone in situ formed from acetylenic esters with hydrazine hydrate at room temperature with isatin and malononitrile is reported. A plausible mechanism is suggested. Catalyst-free conditions along with green solvent system make the process ecofriendly as well as economical. Simple reaction conditions and easy work-up procedure that resulted into simple isolation and purification of products by non-chromatographic methods, that is, by simple recrystallization from methanol as well as novelty are the significant advantages of the present protocol. (C) 2013 Elsevier Ltd. All rights reserved.