One-Pot Cascade Synthesis of Fused Nitrogen-Containing Heterocycles in Aqueous Media – Utility of N-Protective Groups in Intramolecular Diels–Alder Reaction of Furan

Aydin Demircan; Muhammet K. Kandemir; Medine Colak; Muhsin Karaarslan

doi:10.1055/s-0035-1562458

Synthesis, Table of Contents

Synthesis 2016; 48(17): 2873-2880
DOI: 10.1055/s-0035-1562458

paper

One-Pot Cascade Synthesis of Fused Nitrogen-Containing Heterocycles in Aqueous Media – Utility of N-Protective Groups in Intramolecular Diels–Alder Reaction of Furan

Aydin Demircan*

^aDepartment of Chemistry, Nigde University, Kampus, 51240, Nigde, Turkey Email: ademircan@nigde.edu.tr

,

Muhammet K. Kandemir

^aDepartment of Chemistry, Nigde University, Kampus, 51240, Nigde, Turkey Email: ademircan@nigde.edu.tr

,

Medine Colak

^aDepartment of Chemistry, Nigde University, Kampus, 51240, Nigde, Turkey Email: ademircan@nigde.edu.tr

,

Muhsin Karaarslan

^bDepartment of Chemistry, Aksaray University, Kampus, 68000, Aksaray, Turkey

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Abstract

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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.

Key words

cycloaddition - cascade reactions - intramolecular Diels–Alder reaction - heterocycles - furan

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References

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