Related Experiment Video
Updated: Mar 30, 2026

Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
Published on: June 23, 2019
Synthesis of 2-cyclopropyl-3-(5-aryl-1H-pyrazol-3-yl)-1,8-naphthyridine
Mallaiah Bucha1, Laxminarayana Eppakayala2, Thirumala Chary Maringanti3
1Mahatma Gandhi Institute of Technology, Gandipet, Hyderabad, 50075, Telangana, India. mallesh8@gmail.com.
Background:
1,8-Naphthyridine derivatives have attracted considerable attention because the 1,8-naphthyridine skeleton is present in many compounds that have been isolated from natural substances, with various biological activities.
Findings:
N,N-dimethoxy-N-methyl-1,8-naphthyridine-3-carboxamide (1) on reaction with Grignard reagent forms 2-methoxy-1,8-naphthyridine-3-carbaldehyde (2). Compound 2 on reaction with different aromatic aldehydes provided 1-(2-cyclopropyl-1,8-naphthyridin-3-yl)-3-arylprop-2-en-1-ones (3a-e) and these compounds on cyclisation with hydrazine hydrate 99% yielded 2-cyclopropyl-3-(5-aryl-1H-pyrazol-3-yl)-1,8-naphthyridines (4-a-e). Synthesis of the target compounds involved the formation of 4a-e. It was accomplished using Grignard reaction, condensation reaction, and cyclisation reactions. All the synthesized compounds were readily soluble in DMSO. Spectral data of the synthesized compounds were in full agreement with the proposed structures.
Conclusions:
In conclusion, we have developed a simple and an efficient Synthesis of 2-cyclopropyl-3-(5-aryl-1H-pyrazol-3-yl)-1,8-naphthyridine.
Related Concept Videos
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group...
Preparation of Nitriles
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Five-Membered Heterocyclic Aromatic Compounds: Overview
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
