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Synlett 2014; 25(1): 120-122
DOI: 10.1055/s-0033-1340053
DOI: 10.1055/s-0033-1340053
letter
Copper-Catalyzed Protodecarboxylation and Aromatization of Tetrahydro-β-Carboline-3-Carboxylic Acids
Further Information
Publication History
Received: 03 September 2013
Accepted after revision: 30 September 2013
Publication Date:
12 November 2013 (online)
Abstract
An efficient synthetic methodology has been developed to construct aromatic β-carbolines from tetrahydro-β-carboline-3-carboxylic acids by copper-promoted sequential decarboxylation and oxidative aromatization.
Key words
tetrahydro-β-carboline-3-carboxylic acids - decarboxylation - aromatization - copper - aromatic β-carbolineSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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- 17 General Procedure To 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid (1 mmol) in DMF (10 mL) was added CuCl2 (10 mol%) and stirred for 1 h at 130 °C. On completion of the reaction (TLC), H2O (5 mL) was added to the reaction, and the mixture was basified to pH 9 with 1 M NaOH. The aqueous layer was extracted with CH2Cl2 (3 × 20 mL), and the combined organic layers were dried over anhydrous Na2SO4. The CH2Cl2 was evaporated, and the residue was purified by chromatography which afforded pure 9H-pyrido[3,4-b]indole (2a) as a white solid. 1H NMR (500 MHz, DMSO-d 6): δ = 11.63 (1 H, s), 8.89 (d, J = 0.5 Hz, 1 H), 8.31 (d, J = 5.5 Hz, 1 H), 8.2 (d, J = 7.0 Hz, 1 H), 8.09 (dd, J 1 = 0.5 Hz, J 2 = 1.0 Hz, 1 H), 7.60 (d, J = 10.0 Hz, 1 H), 7.55–7.53 (m, 1 H), 7.24–7.21 (m, 1 H). 13C NMR (125 MHz, DMSO-d 6): δ = 140.5, 137.9, 135.9, 133.7, 128.5, 127.6, 121.7, 120.4, 119.4, 114.7, 112.1. GC–MS: 168 [M+].
For reviews on the chemistry and biology of β-carbolines, see: