Tandem Nenitzescu Reaction/Nucleophilic Aromatic Substitution to Form Novel Pyrido Fused Indole Frameworks

被引：5

作者：

Singh, Rashmi ^{[1
,2
]}

Bhatia, Harshita ^{[3
]}

Prakash, Prabhat ^{[4
]}

Debroye, Elke ^{[3
]}

Dey, Swapan ^{[1
]}

Dehaen, Wim ^{[2
]}

机构：

[1] Indian Sch Mines, Indian Inst Technol, Dept Chem, Dhanbad 826004, Bihar, India

[2] Katholieke Univ Leuven, Mol Design & Synth, Dept Chem, Celestijnenlaan 200F, B-3001 Leuven, Belgium

[3] Katholieke Univ Leuven, Mol Imaging & Photon, Dept Chem, Celestijnenlaan 200F, B-3001 Leuven, Belgium

[4] Indian Inst Technol Gandhinagar, Mat Engn, Gandhinagar 382355, Gujarat, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 2021卷 / 34期

基金：

欧洲研究理事会;

关键词：

Enamines; 5-Hydroxyindoles; Nenitzescu reaction; Nucleophilic aromatic substitution; Polycyclic heterocycles; Pyrido (furo) indoles; Quinones; 1ST BIOLOGICAL EVALUATION; PRIVILEGED STRUCTURES; 1-AZA-9-OXAFLUORENES; HETEROARENES; DERIVATIVES; ALKALOIDS; SCAFFOLD;

D O I：

10.1002/ejoc.202100827

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5-Hydroxyindoles are privileged structures that form part of various bioactive compounds. The Nenitzescu reaction of quinones and enamines is one of the most powerful methods to obtain 5-hydroxyindoles. In this work, we have applied the Nenitzescu reaction to 2-(2-chloropyrid-3-yl)benzoquinones. Mixtures of regioisomers were obtained that could be separated in the 4- and 6-substituted analogues, and then cyclized separately in a metal-free base-catalyzed reaction, affording novel tetracyclic indole derivatives. These are indeed the first examples reported in the literature of the linear pyrido[3 ',2 ' : 4,5]furo[3,2-b]indole and angular 1H-pyrido[2 ',3 ' : 4,5]furo[2,3-c]indole systems. The regioselectivity and the yield of the Nenitzescu reaction were found to be dependent on the N-substituent at the enamine. Furthermore, we analyzed the UV-Vis and PL spectra of the new systems, and this was supported by DFT calculations, allowing us to compare the properties of angular compared to linearly shaped compounds.

引用

页码：4865 / 4875

页数：11

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