title: Rapid access to N-(indol-2-yl)amides and N-(indol-3-yl)amides as unexplored pharmacophores.
abstract: Preparation of N-(indol-2-yl)amides and N-(indol-3-yl)amides are scarce in the scientific literature due to unstable intermediates impeding current reported syntheses. We have employed cheap and readily available substrates in the Curtius rearrangement of indole-3-carboxazide to afford N-(indol-3-yl)amides. The reaction is observed for alkyl and aryl carboxylic acids and both N-substituted or 1H-indole derivatives are tolerated. This approach was extended to the preparation of N-(indol-2-yl)amides from the corresponding indole-2-carboxazides.
authors.affiliation: School of Chemistry, University of Sydney, NSW 2006, Australia. michael.kassiou@sydney.edu.au.
authors.forename: Tristan A
authors.initials: TA
authors.lastname: Reekie
authors.affiliation: School of Chemistry, University of Sydney, NSW 2006, Australia. michael.kassiou@sydney.edu.au.
authors.forename: Shane M
authors.initials: SM
authors.lastname: Wilkinson
authors.affiliation: School of Chemistry, University of Sydney, NSW 2006, Australia. michael.kassiou@sydney.edu.au.
authors.forename: Vivian
authors.initials: V
authors.lastname: Law
authors.affiliation: Faculty of Pharmacy, University of Sydney, NSW 2006, Australia.
authors.forename: David E
authors.identifier: http://orcid.org/0000-0002-2635-2990
authors.initials: DE
authors.lastname: Hibbs
authors.affiliation: Faculty of Pharmacy, University of Sydney, NSW 2006, Australia.
authors.forename: Jennifer A
authors.initials: JA
authors.lastname: Ong
authors.affiliation: School of Chemistry, University of Sydney, NSW 2006, Australia. michael.kassiou@sydney.edu.au.
authors.forename: Michael
authors.identifier: http://orcid.org/0000-0002-6655-0529
authors.initials: M
authors.lastname: Kassiou