(4-chlorobenzoyl)(3,4-dihydroisoquinolin-2-ium-2-yl)amide | 1357786-91-4

• 英文名称: (4-chlorobenzoyl)(3,4-dihydroisoquinolin-2-ium-2-yl)amide
• CAS: 1357786-91-4
• 化学式: C₁₆H₁₃ClN₂O
• 分子量: 284.745
• InChiKey: VODJYISUGMDMNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
  None
• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  (4-chlorobenzoyl)(3,4-dihydroisoquinolin-2-ium-2-yl)amide 在 六甲基磷酰三胺 、 dimethylphenyl sulfonium tetrafluoroborate 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以73%的产率得到3-(4-chlorophenyl)-6,7-dihydro-1H-1,5-methanobenzo[g][1,3,4]oxadiazonine
  参考文献：
  名称：

  Ring Enlargement Reaction of C,N-Cyclic-N′-acyl Azomethine Imines with Sulfonium Ylide: An Efficient Synthesis of 3-Benzazepine Derivatives

  摘要：

  Highly efficient formation of 3-benzazepine derivatives has been achieved, based on the ring expansion reaction of C,N-cyclic-N'-acyl azomethine imines with sulfonium ylide generated in situ from the corresponding sulfonium salt. The reactions proceeded smoothly to afford the tricyclic 3-benzazepine derivatives in good to high yields. A wide range of C,N-cyclic N'-acyl azomethine imines were applicable to this reaction.

  DOI：

  10.1021/ol502347n

文献信息

• [5 + 1] Cycloaddition of <i>C,N</i>-Cyclic <i>N</i>′-Acyl Azomethine Imines with Isocyanides
  作者：Takahiro Soeta、Kaname Tamura、Yutaka Ukaji

  DOI：10.1021/ol2034542

  日期：2012.3.2

  A catalyst-free [5 + 1] cycloaddition reaction between isocyanides and C,N-cyclic N′-acyl azomethine imines as the “isocyanophile” leading to novel heterocycles has been developed. These reactions proceeded quickly and cleanly to afford the corresponding imin-1,3,4-oxadiazin-6-one derivatives in high to excellent yields. A wide range of C,N-cyclic N′-acyl azomethine imines and isocyanides were applicable

  已开发出异氰酸酯与作为新异杂环的“异氰酸酯”的C，N-环N'-酰基偶氮甲亚胺亚胺之间的无催化剂[5 +1]环加成反应。这些反应快速而干净地进行，以高到极好的收率得到相应的亚胺-1,3,4-恶二嗪-6-一衍生物。各种各样的C，N-环N'-酰基偶氮甲亚胺和异氰酸酯可用于该反应。
• A three-component reaction of C,N-cyclic N′-acyl azomethine imines, isocyanides, and azide compounds: effective synthesis of 1,5-disubstituted tetrazoles with tetrahydroisoquinoline skeletons
  作者：Takahiro Soeta、Kaname Tamura、Shuhei Fujinami、Yutaka Ukaji

  DOI：10.1039/c3ob27297d

  日期：——

  A multicomponent reaction of isocyanides and C,N-cyclic N′-acyl azomethine imines in the presence of TMSCl and NaN3 leads to tetrazole derivatives. These reactions proceeded cleanly to afford the corresponding 1,5-disubstituted tetrazoles containing a tetrahydroisoquinoline skeleton in high to excellent yields.

  在TMSCl和NaN3的存在下，异氰化物与C,N-环状N'-酰基偶氮甲亚胺的多元反应可得到四唑衍生物。这些反应顺利进行，以高水平至极佳的产率得到了含有四氢异喹啉骨架的1,5-二取代四唑。
• Palladium-catalyzed [3+2] annulation of allenyl carbinol acetates with C,N-cyclic azomethine imines
  作者：Biming Mao、Junya Zhang、Yi Xu、Zhengyang Yan、Wei Wang、Yongjun Wu、Changqing Sun、Bing Zheng、Hongchao Guo

  DOI：10.1039/c9cc06670e

  日期：——

  with azomethine imines has successfully been developed under mild reaction conditions, affording biologically interesting tetrahydropyrazoloisoquinoline derivatives in high to excellent yields and with excellent stereoselectivity. The reaction follows a tandem [3+2] cycloaddition/allylation/elimination of AcOH pathway. Allenyl carbinol acetates also reacted well with in situ generated azomethine imine

  在本文中，成功开发了在温和的反应条件下钯催化的[3 + 2]烯丙乙酸乙酸酯与偶氮甲亚胺的环化反应，提供了生物学上令人感兴趣的四氢吡唑并异喹啉衍生物，具有高到极好的收率，并且具有出色的立体选择性。反应遵循串联的[3 + 2]环加成/烯丙基化/消除AcOH途径。烯丙基甲醇乙酸酯在相似的反应路径下，在Ag（I）/ Pd（0）催化剂的共催化下，还可以与原位生成的甲亚胺亚胺充分反应。
• N-Heterocyclic carbene-catalyzed [2+3] cyclocondensation of α-chloroaldehydes with azomethine imines
  作者：Zhong-Hua Gao、Xiang-Yu Chen、Jin-Tang Cheng、Wei-Lin Liao、Song Ye

  DOI：10.1039/c5cc01238d

  日期：——

  The N-heterocyclic carbene-catalyzed enantioselective [2+3] cyclocondensation of α-chloroaldehydes with azomethine imines was developed to give the corresponding pyrazolidinones in good yields with excellent enantioselectivities.

  N-杂环卡宾催化的α-氯醛与偶氮甲醛亚胺的对映选择性[2+3]环缩合反应已经发展，能够以良好产率和优异对映选择性得到相应的吡唑啉酮。
• 1,3-Dipolar Cycloadditions of 4-Acetoxy Allenoates: Access to 2,3-Dihydropyrazoles, 2,3-Dihydroisoxazoles, and Indolizines
  作者：Falin Li、Jiangfei Chen、Yading Hou、Yujie Li、Xin-Yan Wu、Xiaofeng Tong

  DOI：10.1021/acs.orglett.5b02724

  日期：2015.11.6

  The thermal 1,3-dipolar cycloadditions of 4-acetoxyallenoates 1 with various dipoles have been reported. When azomethine imines and nitrones are used as the 1,3-dipole partner, the corresponding reactions afford 2,3-dihydropyrazole and 2,3-dihydroisoxazole derivatives, respectively. These reactions might proceed via a thermal 1,3-dipolar cycloaddition and the subsequent elimination of HOAc. In addition

  已经报道了4-乙酰氧基脲酸酯1与各种偶极的热1，3-偶极环加成。当将甲亚胺亚胺和硝酮用作1,3-偶极伴侣时，相应的反应分别得到2,3-二氢吡唑和2,3-二氢异恶唑衍生物。这些反应可能通过热的1,3-偶极环加成反应和随后的HOAc消除反应进行。另外，脲基甲酸酯1与原位产生的甲亚胺基团良好反应，其中类似的环加成途径随后是氧化芳构化，以得到吲哚嗪衍生物。