Highly Diastereoselective Synthesis of Polycyclic Indolines through Formal [4+2] Propargylic Cycloaddition of Indoles with Ethynyl Benzoxazinanones

A formal [4+2] propargylic annulation of indoles and pyrrole with ethynyl benzoxazinanones was described. This protocol provides a concise synthesis of tetrahydro‐5H‐indolo[2,3‐b]quinolines and tetrahydro‐3H‐pyrrolo[3,2‐b]quinoline, the core structures of alkaloid frameworks, featuring excellent yie...

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Bibliographic Details
Published inChemistry, an Asian journal Vol. 15; no. 16; pp. 2462 - 2466
Main Authors Shao, Wen, Xu‐Xu, Qing‐Feng, You, Shu‐Li
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 17.08.2020
Subjects
Chemical reactions
Chemistry
Cycloaddition
Heterocyclic compounds
Indoles
indoline
Organic compounds
propargylation
pyrrole
Quinoline
quinone methide
Stereoselectivity
Substrates
Synthesis
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Summary:A formal [4+2] propargylic annulation of indoles and pyrrole with ethynyl benzoxazinanones was described. This protocol provides a concise synthesis of tetrahydro‐5H‐indolo[2,3‐b]quinolines and tetrahydro‐3H‐pyrrolo[3,2‐b]quinoline, the core structures of alkaloid frameworks, featuring excellent yields, high diastereoselectivity, mild conditions and wide substrate scope. A metal‐free formal [4+2] propargylic cycloaddition between aza‐oQMs, which is in situ generated from ethynyl benzoxazinanones assisted by a common Brønsted base, and simple indole derivatives has been developed. This method provides a convenient and practical access to a variety of single diastereoisomeric polycyclic indolines in excellent yields under open‐flask ambient conditions.
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ISSN:1861-4728
1861-471X
DOI:10.1002/asia.202000640