Issue 42, 2014

Synthesis of naphthalene amino esters and arylnaphthalene lactone lignans through tandem reactions of 2-alkynylbenzonitriles

Abstract

Tandem reaction of 2-alkynylbenzonitriles with a Reformatsky reagent turned out to be a novel and efficient approach toward 1-aminonaphthalene-2-carboxylates. Interestingly, with 2-(3-hydroxyprop-1-ynyl)benzonitriles as the substrates, a more sophisticated cascade process occurred to give 9-aminonaphtho[2,3-c]furan-1(3H)-ones in good yields. By using this tandem reaction as a key step, a concise and versatile synthetic strategy for the total synthesis of arylnaphthalene lactone lignans has been developed.

Graphical abstract: Synthesis of naphthalene amino esters and arylnaphthalene lactone lignans through tandem reactions of 2-alkynylbenzonitriles

Supplementary files

Article information

Article type
Communication
Submitted
07 Mar 2014
Accepted
02 Apr 2014
First published
03 Apr 2014

Chem. Commun., 2014,50, 5641-5643

Author version available

Synthesis of naphthalene amino esters and arylnaphthalene lactone lignans through tandem reactions of 2-alkynylbenzonitriles

Y. He, X. Zhang and X. Fan, Chem. Commun., 2014, 50, 5641 DOI: 10.1039/C4CC01738B

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