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Synlett 2014; 25(12): 1781-1785
DOI: 10.1055/s-0034-1378265
DOI: 10.1055/s-0034-1378265
letter
Synthesis of Multisubstituted Tetrahydroquinolines through Aza-Michael/ Michael Addition Catalyzed by Quaternary Ammonium Salt
Authors
Weitere Informationen
Publikationsverlauf
Received: 27. Februar 2014
Accepted after revision: 07. Mai 2014
Publikationsdatum:
05. Juni 2014 (online)
Abstract
Multisubstituted tetrahydroquinolines were obtained in excellent yield from an array of N-[2-(3-oxo-3-phenylprop-1-enyl)phenyl]benzamide derivatives in a reaction catalyzed by quaternary ammonium salt. This method provides an efficient approach to the synthesis of densely substituted tetrahydroquinoline derivatives.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/
10.1055/s-00000083.
- Supporting Information (PDF)
-
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- 17 Synthesis of 6a; Typical Procedure: A mixture of 5a (32.7 mg, 0.01 mmol), K3PO4 (84.9 mg, 0.04 mmol), and BnEt3NCl (2.28 mg, 0.001 mmol) in toluene (4 mL) was stirred at room temperature for 6 h. Upon completion of reaction as indicated by TLC, the solvent was evaporated and the residue was purified by flash chromatography on silica gel to provide the desired product 6a. 1H NMR (400 MHz, CDCl3): δ = 10.47 (s, 1 H), 7.98 (dd, J = 11.9, 4.7 Hz, 4 H), 7.89 (d, J = 8.1 Hz, 1 H), 7.59 (t, J = 7.4 Hz, 1 H), 7.52–7.43 (m, 6 H), 67.43–7.37 (m, 1 H), 7.37–7.27 (m, 4 H), 7.27–7.12 (m, 6 H), 7.09 (d, J = 7.6 Hz, 1 H), 7.00 (dd, J = 11.1, 4.1 Hz, 1 H), 6.93 (t, J = 7.4 Hz, 1 H), 6.68 (d, J = 7.0 Hz, 1 H), 6.39 (d, J = 7.8 Hz, 1 H), 6.15 (d, J = 6.9 Hz, 1 H), 4.41 (dd, J = 11.4, 6.9 Hz, 1 H), 4.26 (t, J = 9.0 Hz, 1 H), 3.63 (dd, J = 18.1, 8.7 Hz, 1 H), 3.43 (dd, J = 18.1, 2.7 Hz, 1 H); 13C NMR (100 MHz, CDCl3): δ = 200.05, 197.45, 170.36, 165.29, 138.67, 136.52, 136.32, 136.27, 135.52, 134.70, 134.43, 133.88, 133.49, 132.59, 131.40, 130.83, 129.17, 128.77, 128.68, 128.50, 128.44, 128.06, 128.01, 127.44, 127.38, 126.96, 126.81, 126.49, 125.66, 125.21, 125.06, 58.14, 55.14, 37.67, 34.79; IR (KBr): 3269, 3059, 2904, 1673, 1597, 1449, 1361, 1226, 972, 755 cm–1; MS (ESI): m/z = 655 [M + H+]; HRMS (ESI): m/z [M + H+] calcd. for C44H35N2O4 +: 655.2586; found: 655.25913.