5-(4-chlorophenyl)indazolo[3,2-b]quinazolin-7(5H)-one | 1370643-38-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-chlorophenyl)indazolo[3,2-b]quinazolin-7(5H)-one
• 英文别名: 5-(4-Chlorophenyl)indazolo[3,2-b]quinazolin-7-one
• CAS: 1370643-38-1
• 化学式: C₂₀H₁₂ClN₃O
• 分子量: 345.788
• InChiKey: FTROUSVKMHFPDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  35.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(4-chlorophenylamino)-2-phenylquinazolin-4(3H)-one 在 氧气 、 palladium diacetate 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.17h， 以75%的产率得到5-(4-chlorophenyl)indazolo[3,2-b]quinazolin-7(5H)-one
  参考文献：
  名称：

  Pd-Catalyzed Intramolecular Aerobic Oxidative C–H Amination of 2-Aryl-3-(arylamino)quinazolinones: Synthesis of Fluorescent Indazolo[3,2-b]quinazolinones

  摘要：

  A palladium-catalyzed intramolecular aerobic oxidative C-H amination of 2-aryl-3-(arylamino)quinazolinones has been developed, providing a variety of substituted indazolo[3,2-b]quinazolinone derivatives in moderate to excellent yields. Preliminary mechanistic studies suggested that a palladacycle dimer could be the key intermediate, which underwent a cascade "rollover" cyclometalation and C-H amination sequence. Furthermore, the potential utility of these products has been demonstrated as a new class of blue fluorophores for fluorescent materials.

  DOI：

  10.1021/ol5026553

文献信息

• A new cascade reaction: concurrent construction of six and five membered rings leading to novel fused quinazolinones
  作者：K. Siva Kumar、P. Mahesh Kumar、V. Sreenivasa Rao、Ahamed A. Jafar、Chandana Lakshmi T. Meda、R. Kapavarapu、Kishore V. L. Parsa、Manojit Pal

  DOI：10.1039/c2ob25296a

  日期：——

  A one-pot cascade reaction has been developed leading to the concurrent construction of six and five membered fused N-heterocyclic rings of indazolo[3,2-b]quinazolinones. The methodology involved the reaction of isatoic anhydride, a hydrazine and o-iodo benzaldehyde in the presence of Pd(PPh3)4 and BINAP in MeCN. The mechanism of this cascade reaction is discussed. A variety of indazolo[3,2-b]quinazolinone derivatives were prepared by using this methodology in good yields, some of which were tested for their PDE4 inhibitory properties in vitro. The dose response and docking study performed using a representative compound is presented.

  本研究开发了一种一锅级联反应，可同时生成吲唑并[3,2-b]喹唑啉酮的六位和五位融合 N-杂环。该方法涉及异酸酐、肼和邻碘苯甲醛在 Pd(PPh3)4 和 BINAP 存在下于 MeCN 中的反应。本文讨论了这一级联反应的机理。利用这种方法制备了多种吲唑并[3,2-b]喹唑啉酮衍生物，产率良好，其中一些衍生物还进行了体外 PDE4 抑制性测试。文中介绍了使用代表性化合物进行的剂量反应和对接研究。
• 一种一锅法合成喹唑啉酮并吲唑衍生物的方法
  申请人：温州大学

  公开号：CN104761558B

  公开（公告）日：2016-09-21

  本发明涉及一种一锅法合成下式(I)所示的喹唑啉酮并吲唑衍生物的方法，所述方法为：以钯化合物作为催化剂，在氧化剂存在下，于复合溶剂中，式(II)化合物与式(III)化合物发生反应，从而得到式(I)衍生物：其中：R1、R2、R3各自独立地选自H、C1‑C6烷基、C2‑C6烯基、C1‑C6烷氧基、卤素、卤代C1‑C6烷基或卤代C1‑C6烷氧基。本发明的所述能够使式(II)与式(III)化合物顺利发生一锅法反应，并能以良好产率得到目的产物，具有很高的理论研究价值和应用价值。
• Copper-catalyzed C–O bond cleavage and cyclization: synthesis of indazolo[3,2-b]quinazolinones
  作者：Rui Qiao、Leping Ye、Kun Hu、Shuling Yu、Weiguang Yang、Miaochang Liu、Jiuxi Chen、Jinchang Ding、Huayue Wu

  DOI：10.1039/c6ob02352e

  日期：——

  of a copper-catalyzed halogen-free protocol to construct indazolo[3,2-b]quinazolinones was developed through sequential inert C–O bond cleavage followed by intramolecular C–N bond formation. This protocol represents an efficient synthetic tool for accessing a more diverse range of functionalized indazolo[3,2-b]quinazolinones. The structure of the newly synthesized indazolo[3,2-b]quinazolinones was unambiguously

  通过依次进行惰性C–O键裂解和随后的分子内C–N键形成过程，开发了构建铜吲哚并[3,2- b ]喹唑啉酮的铜催化无卤方案的第一个实例。该协议代表了一种有效的合成工具，可用于获得更多种类的功能化吲唑并[3,2- b ]喹唑啉酮。通过X射线晶体衍射分析明确地确认了新合成的吲唑并[3，2- b ]喹唑啉酮的结构。
• Copper(I)-Catalyzed Synthesis of 5-Arylindazolo[3,2-<i>b</i>]quinazolin-7(5<i>H</i>)-one via Ullmann-Type Reaction
  作者：Dong-Sheng Chen、Guo-Lan Dou、Yu-Ling Li、Yun Liu、Xiang-Shan Wang

  DOI：10.1021/jo400420b

  日期：2013.6.7

  The treatment of 2-amino-N'-arylbenzohydrazide and o-halogenated benzaldehyde in the presence of CuBr and Cs2CO3 gave 5-arylindazolo[3,2-b]quinazolin-7(5H)-one in high yields. This procedure contains an Ullmann-type reaction and provides an efficient method to construct fused tetracyclic heterocycles.
• Palladium-Catalyzed Cascade Reaction of 2-Amino-<i>N</i>′-arylbenzohydrazides with Triethyl Orthobenzoates To Construct Indazolo[3,2-<i>b</i>]quinazolinones
  作者：Weiguang Yang、Rui Qiao、Jiuxi Chen、Xiaobo Huang、Miaochang Liu、Wenxia Gao、Jinchang Ding、Huayue Wu

  DOI：10.1021/jo5024848

  日期：2015.1.2

  A palladium-catalyzed sequential cyclization/C-H activation cascade reaction of 2-amino-N'-arylbenzohydrazides with triethyl orthobenzoates has been developed, providing indazolo[3,2-b]quinazolinones in good to high yields. Two key intermediates of the reaction, 2-phenyl-3-(phenylamino)quinazolinone and C-H insertion palladacycle, were isolated, and their structures were unambiguously confirmed by X-ray crystallography. This method represents an unprecedented example of a halogen-free protocol to access indazolo[3,2-b]quinazolinones. Moreover, this chemistry also provides a useful tool for the discovery of fluorescent materials.