Issue 4, 2015

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
27 Jan 2015
Accepted
09 Feb 2015
First published
12 Feb 2015

Org. Chem. Front., 2015,2, 394-397

Author version available

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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