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Synthesis 2015; 47(16): 2467-2472
DOI: 10.1055/s-0034-1380696
DOI: 10.1055/s-0034-1380696
paper
One-Pot Synthesis of Novel Cyclopentene-Fused Octahydropyridoquinolines and Octahydrophenanthrolines
Weitere Informationen
Publikationsverlauf
Received: 02. Februar 2015
Accepted after revision: 09. April 2015
Publikationsdatum:
26. Mai 2015 (online)
![](https://www.thieme-connect.de/media/synthesis/201516/lookinside/thumbnails/ss-2015-t0080-op_10-1055_s-0034-1380696-1.jpg)
Abstract
New cyclopentene-fused octahydropyridoquinolines and octahydrophenanthrolines were prepared by a stereoselective three-component cyclocondensation of benzene-1,4-diamine, cyclopenta-1,3-diene, and an aromatic aldehyde. Single-crystal X-ray diffraction data provided evidence for the formation of cyclopentene-fused octahydropyridoquinolines and octahydrophenanthrolines with a syn-planar arrangement of the cyclopentene rings. The cyclocondensation of benzene-1,4-diamine, cyclopenta-1,3-diene, and formaldehyde gave new type of polycyclic compound containing four cyclopentene moieties oriented in a mutually antiplanar manner.
Key words
Diels–Alder reactions - electrophilic aromatic substitutions - heterocycles - polycycles - fused-ring systemsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380696.
- Supporting Information
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References
- 1a Müller TJ. J, D’Souza DM. Pure Appl. Chem. 2008; 80: 609
- 1b Glushkov VA, Tolstikov AG. Russ. Chem. Rev. 2008; 77: 137
- 1c Orru RV. A, de Greef M. Synthesis 2003; 1471
- 1d Ramón DG, Yus M. Angew. Chem. Int. Ed. 2005; 44: 1602
- 2 Kouznetsov VV. Tetrahedron 2009; 65: 2721
- 3 Povarov LS. Russ. Chem. Rev. 1967; 36: 656
- 4 Tolstikov AG, Savchenko RG, Nedopekin DV, Afon’kina SR, Lukina ЕS, Оdinokov VN. Russ. Chem. Bull. 2011; 60: 160
- 5a Mellor JM, Merriman GD, Riviere P. Tetrahedron Lett. 1991; 32: 7103
- 5b Temme O, Laschat S, Fröhlich R, Wibbeling B, Heinze J, Hauser P. J. Chem. Soc., Perkin Trans. 2 1997; 2083
- 5c Temme O, Laschat S. J. Chem. Soc., Perkin Trans. 1 1995; 125
- 5d Yadav JC, Reddy BV. S, Chetia L, Srinivasulu G, Kunwar AC. Tetrahedron Lett. 2005; 46: 1039
- 5e Powell DA, Batey RA. Tetrahedron Lett. 2003; 44: 7569
- 6 Linkert F, Laschat S, Kotila S, Fox T. Tetrahedron 1996; 52: 955
- 7 Grieco PA, Bahsas A. Tetrahedron Lett. 1988; 29: 5855
- 8 Tolstikov AG, Savchenko RG, Lukina ЕS, Afon’kina SR, Nedopekin DV, Khalilov LM, Оdinokov VN. Russ. Chem. Bull. 2013; 62: 2377
- 9 Sheldrick GM. SHELX97 [Includes SHELXS97, SHELXL97 and CIFTAB]: Programs for Crystal Structure Analysis (Release 97-2). Institüt für Anorganische Chemie der Universität Göttingen; Germany: 1998
- 10 Crystallographic data for compounds 3a, 4a, 4b, and 5 have been deposited with the accession numbers CCDC 985712, 1002452, 943834, and 985713, respectively, and can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK, Fax: +44(1223)336033, E-mail: deposit@ccdc.cam.ac.uk, Web site: www.ccdc.cam.ac.uk/conts/retrieving.html.