One-Pot Cascade Synthesis of Fused Nitrogen-Containing Heterocycles in Aqueous Media - Utility of N-Protective Groups in Intramolecular Diels-Alder Reaction of Furan
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Date
2016
Journal Title
Journal ISSN
Volume Title
Publisher
GEORG THIEME VERLAG KG
Access Rights
info:eu-repo/semantics/closedAccess
Abstract
A metal-free, thermal, intramolecular Diels-Alder (IMDA) reaction of furan in aqueous media without the use of microwave irradiation was investigated. Protection of the amine functionality and the cycloaddition reaction were performed as a one-pot, two-component process. Various nitrogen-protecting groups and their electronic and steric effects on the cycloaddition reaction were studied. The protection-intramolecular Diels-Alder reaction sequence proceeds under environmentally benign aqueous conditions, which are tolerated by substrates with a broad range of nitrogen-protecting groups such as benzyloxycarbonyl (Cbz), trityl, tert-butoxycarbonyl (Boc), trifluoroacetyl, tosyl, mesyl, and p-nosyl [(4-nitrophenyl)sulfonyl]. This study allowed the development of a stereoselective, tandem allylamine isomerization-Diels-Alder cycloaddition sequence leading to the rapid assembly of complex nitrogen-containing heterocycles in a simple one-pot process.
Description
Keywords
cycloaddition, cascade reactions, intramolecular Diels-Alder reaction, heterocycles, furan
Journal or Series
SYNTHESIS-STUTTGART
WoS Q Value
Q2
Scopus Q Value
Q1
Volume
48
Issue
17
