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Open AccessArticle

Oxidative Photocyclization of Aromatic Schiff Bases in Synthesis of Phenanthridines and Other Aza-PAHs

1
Department of Advanced Materials and Organic Synthesis, Institute of Chemical Process Fundamentals of the Czech Academy of Sciences, v. v. i., Rozvojová 135, 165 02 Prague 6, Czech Republic
2
Department of Analytical Chemistry, Institute of Chemical Process Fundamentals of the Czech Academy of Sciences, v. v. i., Rozvojová 135, 165 02 Prague 6, Czech Republic
3
Department of Inorganic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 2030, 128 40 Prague 2, Czech Republic
4
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306, USA
*
Authors to whom correspondence should be addressed.
Dedicated to Professor Antonín Lyčka on the occasion of his 70th birthday.
Int. J. Mol. Sci. 2020, 21(16), 5868; https://doi.org/10.3390/ijms21165868
Received: 28 July 2020 / Revised: 11 August 2020 / Accepted: 13 August 2020 / Published: 15 August 2020
The oxidative photocyclization of aromatic Schiff bases was investigated as a potential method for synthesis of phenanthridine derivatives, biologically active compounds with medical applications. Although it is possible to prepare the desired phenanthridines using such an approach, the reaction has to be performed in the presence of acid and TEMPO to increase reaction rate and yield. The reaction kinetics was studied on a series of substituted imines covering the range from electron-withdrawing to electron-donating substituents. It was found that imines with electron-withdrawing substituents react one order of magnitude faster than imines bearing electron-donating groups. The 1H NMR monitoring of the reaction course showed that a significant part of the Z isomer in the reaction is transformed into E isomer which is more prone to photocyclization. The portion of the Z isomer transformed showed a linear correlation to the Hammett substituent constants. The reaction scope was expanded towards synthesis of larger aromatic systems, namely to the synthesis of strained aromatic systems, e.g., helicenes. In this respect, it was found that the scope of oxidative photocyclization of aromatic imines is limited to the formation of no more than five ortho-fused aromatic rings. View Full-Text
Keywords: imines; Schiff bases; photocyclization; phenanthridines; azahelicenes imines; Schiff bases; photocyclization; phenanthridines; azahelicenes
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MDPI and ACS Style

Kos, M.; Žádný, J.; Storch, J.; Církva, V.; Cuřínová, P.; Sýkora, J.; Císařová, I.; Kuriakose, F.; Alabugin, I.V. Oxidative Photocyclization of Aromatic Schiff Bases in Synthesis of Phenanthridines and Other Aza-PAHs. Int. J. Mol. Sci. 2020, 21, 5868. https://doi.org/10.3390/ijms21165868

AMA Style

Kos M, Žádný J, Storch J, Církva V, Cuřínová P, Sýkora J, Císařová I, Kuriakose F, Alabugin IV. Oxidative Photocyclization of Aromatic Schiff Bases in Synthesis of Phenanthridines and Other Aza-PAHs. International Journal of Molecular Sciences. 2020; 21(16):5868. https://doi.org/10.3390/ijms21165868

Chicago/Turabian Style

Kos, Martin; Žádný, Jaroslav; Storch, Jan; Církva, Vladimír; Cuřínová, Petra; Sýkora, Jan; Císařová, Ivana; Kuriakose, Febin; Alabugin, Igor. V. 2020. "Oxidative Photocyclization of Aromatic Schiff Bases in Synthesis of Phenanthridines and Other Aza-PAHs" Int. J. Mol. Sci. 21, no. 16: 5868. https://doi.org/10.3390/ijms21165868

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