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Paper | Regular issue | Vol 34, No. 4, 1992, pp.757-764
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5958
A New Synthetic Method for the Synthesis of Hydroxylated Isoquinolines: Preparation of Methyl 6,7- and 7,8-Dihydroxyisoquinoline-3-carboxylates, Potential Protein-Tyrosine Kinase Inhibitors

Terrence R. Burke, Jr.,* Pamela L. Russ, and Victor E. Marquez

*Laboratory of Medicinal Chemistry, Developmental Therapeutics Program, Division of Cancer Treatment, National Cancer Institute, National Instututes of Health, Bethesda, MD 20892, U.S.A.

Abstract

Synthesis of potential protein-tyrosine kinase inhibitors (6c) and (6e) is presented as a general procedure for the preparation of polyhydroxylated isoquinolines. Key features of the method include selective hydroxyl protection of tetrahydroisoquinolines by O-acylation followed by aromatization using MnO2. Quantitative deprotection of resulting O-acylisoquinolines is achieved using methanolic HCl.