5174-89-0

Usage

Uses

Used in Pharmaceutical Industry:
3-Nitro-1,8-naphthyridin-2-ol is used as an active pharmaceutical ingredient for the development of new drugs, particularly those with antimicrobial and anticancer properties. Its unique structure allows for the design of novel therapeutic agents that can target specific biological pathways and mechanisms.
Used in Organic Synthesis:
3-Nitro-1,8-naphthyridin-2-ol is used as a key intermediate in the synthesis of various heterocyclic compounds. Its versatile chemical properties enable the creation of a wide range of complex organic molecules, which can be further utilized in various applications, including pharmaceuticals, agrochemicals, and materials science.
Used in Research and Development:
3-Nitro-1,8-naphthyridin-2-ol is used as a research compound for studying its potential biological activities and exploring its applications in various fields. Its unique structure and properties make it an attractive candidate for further investigation, with the potential to uncover new insights and applications in the fields of chemistry and biology.

Upstream product

• 15992-83-3 [1,8]naphthyridin-2-ylamine 
• 7521-41-7 2-Aminonicotinaldehyde 

Relevant academic research and scientific papers

Direct one-pot synthesis of 3-nitroquinolin-2(1H)-one via H2O/AcOH system: An improvement to classical Friedlander reaction

Quinolin-2(1H)-ones and their derivatives have attracted considerable attention because of their extensive applications in the field of pharmaceuticals, agricultural and dye chemistry. In contrast to the existed synthetic methods, herein we present the one-pot cascade reaction of 1,1-dimeoxyth-2-nitroethene and 2-aminobenzaldehydes which is catalyst-free and via eco-friendly H2O/AcOH solvent, achieving 3-nitroquinolin-2(1H)-ones in moderate to excellent yields. Importantly, this concise and versatile protocol is a potential improvement to the traditional Friedlander reaction.

Methylamination of some 3,6-dinitro-1,8-naphthyridines with liquid methylamine - potassium permanganate

3,6-Dinitro-1,8-naphthyridine and its 2-substituted derivatives are dehydro-methylaminated with the solution of potassium permanganate in liquid methylamine (LMA-PP) to the corresponding mono- or mono- and bis(methylamino)-3,6-dinitro-1,8-naphthyridines. In the case of 2-chloro- and 2-methoxy-3,6-dinitro-1,8-naphthyridine the replacement of chloro and methoxy substituents by the NHCH3 group occurs as well. Quantum-chemical calculations indicate the reactions to be controlled by the interaction of the frontal molecular orbitals (FMO) of the reagents. Moreover the heats of formation of intermediary methylamino-σ-adducts and transition states are calculated for the reaction studied. The calculations show satisfactory agreement between calculated and observed results. A convenient synthesis of some 2-substituted-3,6-dinitro-1,8-naphthyridines is reported.