Synthesis 2015; 47(16): 2467-2472
DOI: 10.1055/s-0034-1380696
paper
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of Novel Cyclopentene-Fused Octahydropyridoquinolines and Octahydrophenanthrolines

Alexander G. Tolstikov
Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, pr. Oktyabrya 141, 450075 Ufa, Russian Federation   Email: ecdysona@gmail.com
,
Rimma G. Savchenko*
Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, pr. Oktyabrya 141, 450075 Ufa, Russian Federation   Email: ecdysona@gmail.com
,
Elena S. Lukina
Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, pr. Oktyabrya 141, 450075 Ufa, Russian Federation   Email: ecdysona@gmail.com
,
Regina M. Limantseva
Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, pr. Oktyabrya 141, 450075 Ufa, Russian Federation   Email: ecdysona@gmail.com
,
Denis V. Nedopekin
Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, pr. Oktyabrya 141, 450075 Ufa, Russian Federation   Email: ecdysona@gmail.com
,
Leonard M. Khalilov
Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, pr. Oktyabrya 141, 450075 Ufa, Russian Federation   Email: ecdysona@gmail.com
,
Ecaterina S. Meshcheriakova
Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, pr. Oktyabrya 141, 450075 Ufa, Russian Federation   Email: ecdysona@gmail.com
,
Victor N. Odinokov
Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, pr. Oktyabrya 141, 450075 Ufa, Russian Federation   Email: ecdysona@gmail.com
› Author Affiliations
Further Information

Publication History

Received: 02 February 2015

Accepted after revision: 09 April 2015

Publication Date:
26 May 2015 (online)


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.

Supporting Information

 
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