quino[2',3':3,4]pyrrolo[2,1-b]quinazolin-13-methoxy-11-one | 244616-84-0

• 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: quino[2',3':3,4]pyrrolo[2,1-b]quinazolin-13-methoxy-11-one
• 英文别名: luotonin E；7-methoxyluotonin A；12-methoxy-3,11,21-triazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,13,15,17,19-nonaen-10-one
• CAS: 244616-84-0
• 化学式: C₁₉H₁₃N₃O₂
• 分子量: 315.331
• InChiKey: NUWZAJDJERBAHJ-UHFFFAOYSA-N

物化性质

• 熔点：
  225-227 °C(Solv: benzene (71-43-2))
• 沸点：
  523.5±60.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-formylquinoline-2-carbonitrile 在 乙酸酐 、 溶剂黄146 作用下， 生成 quino[2',3':3,4]pyrrolo[2,1-b]quinazolin-13-methoxy-11-one
  参考文献：
  名称：

  A Concise and Convergent Synthesis of Luotonin B and E

  摘要：

  开发了一种简洁且高度收敛的实践合成方法，以优异的产率在一锅法中制备拓扑异构酶1抑制剂骆驼宁B。在酸性条件下，通过2-氰基喹啉-3-醛或2-氰基喹啉-3-半缩醛与邻甲氧基苯甲酸甲酯的级联环化反应构建了骆驼宁B的C环和D环。随后，通过酸催化的醚化反应将骆驼宁B转化为骆驼宁E。

  DOI：

  10.1055/s-0030-1259098

文献信息

• A catalyst-free rapid, practical and general synthesis of 2-substituted quinazolin-4(3H)-ones leading to luotonin B and E, bouchardatine and 8-norrutaecarpine
  作者：K. Raghavendra Rao、Ramamohan Mekala、Akula Raghunadh、Suresh Babu Meruva、S. Praveen Kumar、Dipak Kalita、Eppakayala Laxminarayana、Bagineni Prasad、Manojit Pal

  DOI：10.1039/c5ra10928k

  日期：——

  quinazolin-4(3H)-one ring using formamide as an efficient ammonia precursor and PEG-400 as an effective solvent. The methodology afforded various 2-substituted quinazolin-4(3H)-one derivatives in good yield via a three-component reaction of isatoic anhydride, aldehydes and formamide in air. This single methodology was extended successfully to the synthesis of several alkaloids e.g. leutonin B and E, bouchardatine

  已经开发出一种非常快速但无微波/超声波/无催化剂的方法，用于使用甲酰胺作为有效的氨前体和PEG-400作为有效的溶剂来构建喹唑啉-4（3 H）-环。该方法通过在空气中通过等角酸酐，醛和甲酰胺的三组分反应，以高收率获得了各种2-取代的喹唑啉-4（3 H）-一衍生物。该单一方法成功地扩展到了几种生物碱的合成，例如，白蛋白B和E，布加达汀和8-去甲太卡品。
• A concise approach to substituted Quinazolin-4(3H)-one natural products catalyzed by Iron(III) Chloride
  作者：Mekala Ramamohan、Kamaraju Raghavendrarao、Regati Sridhar、Gudimalla Nagaraju、Kothapally Bannoath Chandrasekhar、Sarva Jayapraksh

  DOI：10.1016/j.tetlet.2016.02.030

  日期：2016.3

  A novel and efficient method for the synthesis of various Quinazolin-4(3H)-one natural products was developed utilizing Iron(III) Chloride catalyzed reaction as a key step. Circumdatin H, Bouchardatine, 8-Norrutaecarpine and, Luotonin B and E are few natural products synthesized by this methodology.

  利用氯化铁（III）催化反应作为关键步骤，开发了一种新颖高效的合成各种喹唑啉-4（3 H）-天然产物的方法。Circumdatin H，Bouchardatine，8-Norrutaecarpine以及Luotonin B和E很少是通过这种方法合成的天然产物。
• TBAHS-Catalyzed Synthesis of 2-Dihydroquinazolin-2-ylquinoline: An Efficient and Practical Synthesis of Naturally Occurring Alkaloids Luotonin A, B, and E
  作者：Lingaiah Nagarapu、Hanmant Gaikwad、Rajashaker Bantu

  DOI：10.1055/s-0032-1316537

  日期：2012.7

  phase-transfer catalyst (TBAHS) in semi-aqueous phase, followed by Mitsunobu cyclization as key steps for an efficient and practical synthesis of naturally occurring alkaloids luotonin A, B, and E starting from o-nitrobenzaldehyde is reported. The new approach presents the advantage of a shorter route with high overall yield (57%, 45%, and 37%, respectively) and ease of operation.

  在半水相中使用相转移催化剂 (TBAHS) 合成 2-二氢喹唑啉-2-基喹啉，然后以光信环化作为关键步骤，以有效且实用地合成天然生物碱 luotonin A、B 和 E 为起始原料来自邻硝基苯甲醛的报道。新方法的优势在于路线较短、总收率高（分别为 57%、45% 和 37%）且易于操作。
• Iodine-mediated electrochemical C(sp³)–H cyclization: the synthesis of quinazolinone-fused N-heterocycles
  作者：Yan Zhang、Zhenghong Zhou、Zhibin Li、Kangfei Hu、Zhenggen Zha、Zhiyong Wang

  DOI：10.1039/d1cc05865g

  日期：——

  An efficient iodine-mediated electrochemical synthesis for functionalized quinazolinone-fused N-heterocycles was developed. The reaction is scalable, metal-free and chemical oxidant-free.

  一种高效的碘介导的电化学合成方法，用于合成功能化的喹唑啉并N-杂环化合物。该反应可扩展，无金属和无化学氧化剂。
• FeCl₃/KI‐Catalyzed Tandem Oxidative Cyclization for Switchable Total Synthesis of Luotonin A, B and Derivatives
  作者：Ying‐Chun Song、Ming‐Xuan Wang、Yun‐Ying Yi、Yu‐Ting Liu、Wen‐Xin Zhang、Zi‐Yue Wang、Yuan‐Yuan Sun、An‐Xin Wu、Yan‐Ping Zhu

  DOI：10.1002/adsc.202301322

  日期：2024.3.19

  A total synthesis strategy was developed for the synthesis of luotonin A, B and their analogues using synergistic FeCl3/KI-catalyzed oxidative cyclization. This protocol utilizes cheap and widely available N-propargyl 2-methyl-quinazolinones and arylamines under mild conditions, and it has a wide substrate scope and high atom economy. Different natural products (luotonin A, B and derivatives) can be

  开发了利用协同 FeCl3/KI 催化氧化环化合成洛豆素 A、B 及其类似物的全合成策略。该方案在温和条件下利用廉价且广泛使用的N-炔丙基2-甲基喹唑啉酮和芳胺，具有较宽的底物范围和较高的原子经济性。不同的天然产物（洛豆素 A、B 和衍生物）可以通过独特的可切换方法合成。从洛调色素B到洛调色素E的进一步转化以及天然产物的结构修饰证明了该方法的潜在应用。此外，还可以用所报道的方案修改喜树碱以提供羟基取代的产物。