Three-step synthesis of Ethyl Canthinone-1-carboxylates from ethyl 4-bromo-6-methoxy-1,5-naphthyridine-3-carboxylate via a Pd-catalyzed Suzuki-Miyaura coupling and a Cu-catalyzed amidation reaction [corrected]

Heraklidia A Ioannidou; Aaron Martin; Andreas Gollner; Panayiotis A Koutentis

doi:10.1021/jo200824b

Three-step synthesis of Ethyl Canthinone-1-carboxylates from ethyl 4-bromo-6-methoxy-1,5-naphthyridine-3-carboxylate via a Pd-catalyzed Suzuki-Miyaura coupling and a Cu-catalyzed amidation reaction [corrected]

J Org Chem. 2011 Jun 17;76(12):5113-22. doi: 10.1021/jo200824b. Epub 2011 May 25.

Authors

Heraklidia A Ioannidou¹, Aaron Martin, Andreas Gollner, Panayiotis A Koutentis

Affiliation

¹ Department of Chemistry, University of Cyprus, P.O. Box 20537, 1678 Nicosia, Cyprus.

PMID: 21563779
DOI: 10.1021/jo200824b

Abstract

Ethyl canthin-6-one-1-carboxylate (1b) and nine analogues 1c-k were prepared from readily prepared ethyl 4-bromo-6-methoxy-1,5-naphthyridine-3-carboxylate (2b) via a three-step non-classical approach that focused on construction of the central pyrrole (ring B) using Pd-catalyzed Suzuki-Miyaura coupling followed by Cu-catalyzed C-N coupling. Furthermore, treatment of the ethyl canthinone-1-carboxylate 1b with NaOH in DCM/MeOH (9:1) gave the canthin-6-one-1-carboxylic acid (6) in high yield. All compounds are fully characterized.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amination
Bromine Compounds / chemistry*
Carboxylic Acids / chemical synthesis*
Catalysis
Copper / chemistry*
Hydrolysis
Molecular Structure
Naphthyridines / chemistry*
Palladium / chemistry*

Substances

Bromine Compounds
Carboxylic Acids
Naphthyridines
Palladium
Copper