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Kamlah, Alexandra; Lirk, Florian; Bracher, Franz (2016): A new approach to 1-substituted β-carbolines and isoquinolines utilizing tributyl[(Z)-2-ethoxyvinyl]stannane as a C-3,C-4 building block. In: Tetrahedron, Vol. 72, No. 6: pp. 837-845
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Starting from readily available indole-2-carboxylic acids, 1-substituted beta-carbolines (among them the alkaloids harmane and isoharmine) are readily obtained via the corresponding 2-acylindoles, bromination at C-3, followed by a one-pot Stille cross-coupling with tributyl[(Z)-2-ethoxyvinyl]stannane, and ring closure with ammonium acetate. 1-Substituted isoquinolines are available in an analogous manner starting from 2-bromobenzoic acid. (C) 2015 Elsevier Ltd. All rights reserved.