{"title":"Synthesis of Nitro‐Substituted Quinolinamines via Cascade Annulations of Hetero‐2‐Alkynyl‐3‐Carbonitriles","authors":"Saurav Kumar, Neha Sharma, Sachin Kumar, Anil Kumar","doi":"10.1002/ajoc.70524","DOIUrl":null,"url":null,"abstract":"<div><div>Quinolinamines are one of the important class of compounds in terms of their biological activity and industrial applications. In this study, we have disclosed transition‐metal‐free synthesis of novel nitro‐substituted quinolinamines. This is the only report that allows the synthesis of quinolines having functionalities at benzene ring instead of pyridine ring. This transformation is compatible with aliphatic, aromatic as well as heteroaromatic substitution on alkynes. In addition, late‐stage modification of some biologically relevant molecules and natural products is disclosed. Furthermore, DFT study was performed to check potential application of the experimental synthesis. Geometrical properties, HOMO‐LUMO analysis, Global reactivity calculations, MEP maps and NLO properties were studied. In addition, docking was done by taking CDK2 protein (PDB ID: 3PXQ) to obtain a preliminary assessment of their potential biological interactions. The docking results showed significantly negative binding affinities reflecting the compounds strong binding with the receptor. Overall, the computational studies provide theoretical insights into the electronic, optical, and biological characteristics of the synthesized compounds and support future experimental evaluation of their potential applications.</div></div><div>Quinolinamines are one of the important class of compounds in terms of their biological activity and industrial applications. In this study, we have disclosed transition‐metal‐free synthesis of novel nitro‐substituted quinolinamines. This is the only report that allows the synthesis of quinolines having functionalities at benzene ring instead of pyridine ring. This transformation is compatible with aliphatic, aromatic as well as heteroaromatic substitution on alkynes. In addition, late‐stage modification of some biologically relevant molecules and natural products is disclosed. Furthermore, DFT study was performed to check potential application of the experimental synthesis. Geometrical properties, HOMO‐LUMO analysis, Global reactivity calculations, MEP maps and NLO properties were studied. In addition, docking was done by taking CDK2 protein (PDB ID: 3PXQ) to obtain a preliminary assessment of their potential biological interactions. The docking results showed significantly negative binding affinities reflecting the compounds strong binding with the receptor. Overall, the computational studies provide theoretical insights into the electronic, optical, and biological characteristics of the synthesized compounds and support future experimental evaluation of their potential applications.</div><div>A transition‐metal‐free approach for the synthesis of novel nitro‐substituted quinolinamines from diverse alkynes (aliphatic, aromatic, and heteroaromatic) was reported. The method enables late‐stage functionalization of biologically relevant molecules and natural products. DFT studies provide insights into geometry, HOMO–LUMO characteristics, global reactivity, MEP, and NLO properties of the synthesized compounds. \n<span><figure><span><img><ol><li><span><span>Download: <span>Download high-res image (84KB)</span></span></span></li><li><span><span>Download: <span>Download full-size image</span></span></span></li></ol></span></figure></span></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 8","pages":"Article e70524"},"PeriodicalIF":2.3000,"publicationDate":"2026-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Asian Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2193580726002394","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2026/9/10 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Quinolinamines are one of the important class of compounds in terms of their biological activity and industrial applications. In this study, we have disclosed transition‐metal‐free synthesis of novel nitro‐substituted quinolinamines. This is the only report that allows the synthesis of quinolines having functionalities at benzene ring instead of pyridine ring. This transformation is compatible with aliphatic, aromatic as well as heteroaromatic substitution on alkynes. In addition, late‐stage modification of some biologically relevant molecules and natural products is disclosed. Furthermore, DFT study was performed to check potential application of the experimental synthesis. Geometrical properties, HOMO‐LUMO analysis, Global reactivity calculations, MEP maps and NLO properties were studied. In addition, docking was done by taking CDK2 protein (PDB ID: 3PXQ) to obtain a preliminary assessment of their potential biological interactions. The docking results showed significantly negative binding affinities reflecting the compounds strong binding with the receptor. Overall, the computational studies provide theoretical insights into the electronic, optical, and biological characteristics of the synthesized compounds and support future experimental evaluation of their potential applications.
Quinolinamines are one of the important class of compounds in terms of their biological activity and industrial applications. In this study, we have disclosed transition‐metal‐free synthesis of novel nitro‐substituted quinolinamines. This is the only report that allows the synthesis of quinolines having functionalities at benzene ring instead of pyridine ring. This transformation is compatible with aliphatic, aromatic as well as heteroaromatic substitution on alkynes. In addition, late‐stage modification of some biologically relevant molecules and natural products is disclosed. Furthermore, DFT study was performed to check potential application of the experimental synthesis. Geometrical properties, HOMO‐LUMO analysis, Global reactivity calculations, MEP maps and NLO properties were studied. In addition, docking was done by taking CDK2 protein (PDB ID: 3PXQ) to obtain a preliminary assessment of their potential biological interactions. The docking results showed significantly negative binding affinities reflecting the compounds strong binding with the receptor. Overall, the computational studies provide theoretical insights into the electronic, optical, and biological characteristics of the synthesized compounds and support future experimental evaluation of their potential applications.
A transition‐metal‐free approach for the synthesis of novel nitro‐substituted quinolinamines from diverse alkynes (aliphatic, aromatic, and heteroaromatic) was reported. The method enables late‐stage functionalization of biologically relevant molecules and natural products. DFT studies provide insights into geometry, HOMO–LUMO characteristics, global reactivity, MEP, and NLO properties of the synthesized compounds.
期刊介绍：
Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC)
The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.
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