Related Experiment Video
Updated: Jun 23, 2025

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Utilization of DMSO as a solvent-cum-reactant: synthesis of fused 2-aryl-4-methylquinolines
Sabina Yashmin1, Karthik A M1, Abu Taleb Khan1
1Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati-781039, India. atk@iitg.ac.in.
Abstract:
Herein, we disclose the synthesis of a variety of disubstituted fused quinoline, such as 4-methyl-2-arylbenzo[h]quinolines (3a-j), 1-methyl-3-arylbenzo[f]quinolines (3k-r), 1-methyl-3-arylnaphtho[2,3-f]quinolines (3s-x), and 2-aryl-5,7-dimethoxy-4-methylquinolines (4a-c), derivatives from the reaction of an aryl aldehyde with 1-naphthylamine (1a), 2-naphthylamine (1b), 2-aminoanthracene (1c) and 3,5-dimethoxyaniline (1d), respectively, at 80 °C in the presence of 30 mol% (±)-10-camphorsulfonic acid ((±)-CSA) using DMSO as the solvent-cum-reactant. DMSO molecules regioselectively incorporate three carbon atoms into the target molecule in this distinct reaction. The other advantages of the present protocol are that it can be performed under mild reaction conditions and does not require metal catalysts, additional additives or oxidants.
Related Concept Videos
Preparation and Reactions of Sulfides
Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
