Construction of tetrahydrobenzo[f]quinoline scaffolds via polar [4+2]-Cycloaddition reaction with arynes as dienophiles

TitleConstruction of tetrahydrobenzo[f]quinoline scaffolds via polar [4+2]-Cycloaddition reaction with arynes as dienophiles
Publication TypeJournal Article
Year of Publication2022
AuthorsPandya, VG, Mhaske, SB
JournalTetrahedron Letters
Volume101
Pagination153901
Date PublishedJUL
Type of ArticleArticle
ISSN0040-4039
KeywordsAryne, Diels-Alder, Diene, Tetrahydrobenzo[ f ]quinoline
Abstract

A transition-metal-free route has been developed for the direct synthesis of biologically significant tetrahydrobenzo[f]quinoline scaffolds. The reaction features polar [4 + 2] Diels-Alder cycloaddition reaction of arynes with a well-designed diene N-Boc protected vinyl tetrahydropyridine, followed by the isomerisation of the double bond leading to the formation of tetrahydrobenzo[f]quinoline scaffolds in good to moderate yields.

DOI10.1016/j.tetlet.2022.153901
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.032

Divison category: 
Organic Chemistry
Database: 
Web of Science (WoS)

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