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Issue 4, 2015
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One pot cascade synthesis of fused heterocycles from furan-tethered terminal alkynes and aldehydes in the presence of amines and CuBr

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Abstract

A novel one-pot protocol for the construction of complex heterocycles through furan tethered terminal alkynes, aldehydes, amines and CuBr upon heating has been developed, giving the cycloadducts in moderate to high yields along with moderate to good regioselectivities. The reactions proceed through a two-component domino reaction including allenation and subsequent intramolecular Diels–Alder reaction. A wide range of aliphatic or aromatic aldehydes and furan tethered terminal alkynes are well-tolerated, enriching the chemistry of the intramolecular Diels–Alder reaction related to furan.

Graphical abstract: One pot cascade synthesis of fused heterocycles from furan-tethered terminal alkynes and aldehydes in the presence of amines and CuBr

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Publication details

The article was received on 27 Jan 2015, accepted on 09 Feb 2015 and first published on 12 Feb 2015


Article type: Research Article
DOI: 10.1039/C5QO00033E
Citation: Org. Chem. Front., 2015,2, 394-397
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    One pot cascade synthesis of fused heterocycles from furan-tethered terminal alkynes and aldehydes in the presence of amines and CuBr

    Y. Zhang, J. Hao and M. Shi, Org. Chem. Front., 2015, 2, 394
    DOI: 10.1039/C5QO00033E

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