Počet záznamů: 1
Oxidative Photocyclization of Aromatic Schiff Bases in Synthesis of Phenanthridines and Other Aza-PAHs†.
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SYSNO ASEP 0531607 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Oxidative Photocyclization of Aromatic Schiff Bases in Synthesis of Phenanthridines and Other Aza-PAHs†. Tvůrce(i) Kos, Martin (UCHP-M) RID, ORCID, SAI
Žádný, Jaroslav (UCHP-M) RID, SAI, ORCID
Storch, Jan (UCHP-M) RID, ORCID, SAI
Církva, Vladimír (UCHP-M) RID, ORCID, SAI
Cuřínová, Petra (UCHP-M) RID, SAI, ORCID
Sýkora, Jan (UCHP-M) RID, ORCID, SAI
Císařová, I. (CZ)
Kuriakose, F. (US)
Alabugin, I.V. (US)Číslo článku 5868 Zdroj.dok. International Journal of Molecular Sciences. - : MDPI
Roč. 21, č. 16 (2020)Poč.str. 15 s. Jazyk dok. eng - angličtina Země vyd. CH - Švýcarsko Klíč. slova imines ; schiff bases ; photocyclization Vědní obor RIV CC - Organická chemie Obor OECD Organic chemistry CEP GA17-02578S GA ČR - Grantová agentura ČR GA20-19353S GA ČR - Grantová agentura ČR Způsob publikování Open access Institucionální podpora UCHP-M - RVO:67985858 UT WOS 000565149200001 EID SCOPUS 85089671665 DOI 10.3390/ijms21165868 Anotace 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. Pracoviště Ústav chemických procesů Kontakt Eva Jirsová, jirsova@icpf.cas.cz, Tel.: 220 390 227 Rok sběru 2021 Elektronická adresa https://www.mdpi.com/1422-0067/21/16/5868
Počet záznamů: 1