One-Pot Site-Selective Sonogashira Cross-Coupling–Heteroannulation of the 2-Aryl-6,8-Dibromoquinolin-4(1H)-Ones: Synthesis of Novel 6-H-Pyrrolo[3,2,1-ij]Quinolin-6-Ones-Reference-Cited by-同舟云学术

One-Pot Site-Selective Sonogashira Cross-Coupling–Heteroannulation of the 2-Aryl-6,8-Dibromoquinolin-4(1H)-Ones: Synthesis of Novel 6-H-Pyrrolo[3,2,1-ij]Quinolin-6-Ones

Published:2014-09 Issue:9 Volume:38 Page:535-538
ISSN:1747-5198
Container-title:Journal of Chemical Research
language:en
Short-container-title:Journal of Chemical Research

Author:

Mphahlele Malose J.¹,Oyeyiola Felix A.¹

Affiliation:

1. Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, PO Box 392, Pretoria 0003, South Africa

Abstract

The 2-aryl-6,8-dibromoquinolin-4(1 H)-ones were subjected to site-selective Sonogashira cross-coupling with terminal acetylenes as models for C sp2-C sp bond formation in the presence of Pd/C–PPh3 and CuI as catalysts and K2CO3 as a base in dioxane to afford the 2-substituted 4-aryl-8-bromo-4 H-pyrrolo[3,2,1- ij]quinolin-6-ones. These were, in turn, subjected to Suzuki–Miyaura cross-coupling with 4-fluorophenylboronic acid as coupling partner to afford the 2-substituted 4,8-diaryl-4 H-pyrrolo[3,2,1- ij]quinolin-6-ones.

Publisher

SAGE Publications

Subject

General Chemistry

Link

http://journals.sagepub.com/doi/pdf/10.3184/174751914X14097554893763

Reference19 articles.

1. Synthesis, Structure-Activity Relationships, and Pharmacological Evaluation of Pyrrolo[3,2,1-ij]quinoline Derivatives: Potent Histamine and Platelet Activating Factor Antagonism and 5-Lipoxygenase Inhibitory Properties. Potential Therapeutic Application in Asthma

2. Pyrrolo[3,2,1- ij ]quinoline derivatives, a 5-HT 2c receptor agonist with selectivity over the 5-HT 2a receptor: potential therapeutic applications for epilepsy and obesity

3. Tricyclic amides: a new class of systemic fungicides active against rice blast disease

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5. Palladium Catalysed Coupling of Iodoquinolines and Acetylenes -- A Novel Entry to the Pyrrolo[3,2,1-ij]quinoline Nucleus

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1. Crystal structure of 8-bromo-6-oxo-2-phenyl-6H-pyrrolo[3,2,1-ij]quinoline-5-carbaldehyde, C18H11BrNO2;Zeitschrift für Kristallographie - New Crystal Structures;2019-09-25

2. Vilsmeier–Haack reaction of 7-acetyl-2-arylindoles: a convenient method for the synthesis of 6-oxo-6H-pyrrolo[3,2,1-ij]quinoline-1,5-dicarbaldehydes;Organic & Biomolecular Chemistry;2019

3. Copper-Catalyzed Aza-Michael Addition of 2-Aminobenzoate to β-Substituted α,β-Unsaturated Ketones: One-Pot Synthesis of 3-Carbonyl-2-Substituted Quinolin-4(1H)-ones;The Journal of Organic Chemistry;2018-02-09

4. ChemInform Abstract: One-Pot Site-Selective Sonogashira Cross-Coupling-Heteroannulation of the 2-Aryl-6,8-dibromoquinolin-4(1H)-ones: Synthesis of Novel 6-H-Pyrrolo[3,2,1-ij]quinolin-6-ones.;ChemInform;2015-03-19