Issue 18, 2015

Mild one-pot Horner–Wadsworth–Emmons olefination and intramolecular N-arylation for the syntheses of indoles, all regio-isomeric azaindoles, and thienopyrroles

Abstract

The syntheses of various N-protected aromatic-ring fused pyrrole-2-carboxylate derivatives have been accomplished using mild one-pot Horner–Wadsworth–Emmons olefination and Cu-catalyzed intramolecular N-arylation reactions. The optimized mild one-pot reaction conditions of various 2-bromo arylcarboxaldehydes with commercially available N-protected phosphonoglycine trimethylesters gave the desired aromatic-ring fused pyrrole-2-carboxylates, such as substituted indole-, all regio-isomeric azaindole-, and thienopyrrole-2-carboxylates, in good to excellent yields. These conditions showed broad substrate compatibility, without the loss of the protecting group.

Graphical abstract: Mild one-pot Horner–Wadsworth–Emmons olefination and intramolecular N-arylation for the syntheses of indoles, all regio-isomeric azaindoles, and thienopyrroles

Supplementary files

Article information

Article type
Paper
Submitted
17 Mar 2015
Accepted
25 Mar 2015
First published
25 Mar 2015

Org. Biomol. Chem., 2015,13, 5131-5138

Author version available

Mild one-pot Horner–Wadsworth–Emmons olefination and intramolecular N-arylation for the syntheses of indoles, all regio-isomeric azaindoles, and thienopyrroles

J. H. Choi and H. J. Lim, Org. Biomol. Chem., 2015, 13, 5131 DOI: 10.1039/C5OB00528K

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