Picosecond dynamics of singlet excited states of oxotetrahydrobenzo[c]phenanthridine in protic and aprotic solvents

Synthesis of Benzoacridines and Benzophenanthridines by Regioselective Pd‐Catalyzed Cross‐Coupling Reactions Followed by Acid‐Mediated Cycloisomerizations

“…Proflavine (a Rev inhibitor),, aminacrine (antibacterial activity), and ethacridine (antibacterial activity) as well as NK109 (antitumor activity), Ethidium (antitumor activity) and Fagaronine (antileukemic activity) represent pharmacologically significant acridines or phenanthridines (Figure ). Furthermore, such substances have been applied in the chemical industries as pigments or dyes and are expected to be promising candidates for the development of organic semiconductors …”

“…In this regard, many studies have been focused on the development of efficient synthetic methodologies for the synthesis of such compounds. Reported synthetic strategies mainly rely on C–H functionalizations,, reductions, dehydrations, intermolecular annulations, intramolecular cyclizations and other methods . However, the applicability of those methods is often limited with regard to the preparative scope.…”

Mn(iii)-mediated reactions of 2-isocyanobiaryl with 1,3-dicarbonyl compounds: efficient synthesis of 6-alkylated and 6-monofluoro-alkylated phenanthridines

“…Phenanthridines are significant skeleton compounds, 1 which exhibit interesting and important biological activities, pharmacological properties 2 and optoelectronic applications. 3 Meanwhile, it is well-known that the introduction of fluorine can influence the physical, chemical, and biological properties of a compound. 4 Recently, Chatani's group has reported the synthesis of phenanthridine derivatives by Mn(acac) 3 mediated annulation of 2-isocyanobiphenyls with arylboronic acid.…”

Substituent‐Guided Switch between CH Activation and Decarboxylative Cross‐Coupling during Palladium/Copper‐Catalyzed Cascade Reactions of 2‐Aminobenzoates with 2‐Haloarylaldehydes

“…Although the preformed benzoimines have been used for the synthesis of phenanthridines by C À H activation/C À C cross-coupling, [14] to the best of our knowledge this constitutes the first example of cascade aldimine formation/CÀH activation/CÀC cross-coupling for the synthesis of phenanthridine. Given the significance of CÀH activation [15] and the importance of phenanthridine-based compounds in medicinal and materials chemistry for their biological activities [16] and optoelectronic properties, [17] we were motivated to study the scope of the reaction in detail.…”

“…To examine the scope of the tandem imination/CÀH activation reaction, various potassium 2-aminobenzoates (1 a-e) and 2-bromobenzaldehydes (2 A-E) were treated under the optimized conditions and the results are presented in Scheme 3. All reactions of potassium 2-aminobenzoate (1 a) with differently substituted 2-bromobenzaldehydes (2 B-E) proceeded smoothly to afford the respective products (4 aB In our continuing interest for the synthesis of pyrazole-annulated ring systems, [17] we next investigated several substituted 4-iodo-3-pyrazolecarbaldehydes as the starting materials in the protocol. Accordingly, aldehydes 8 A-D were treated with potassium 2-aminobenzoate (1 a) under the standardized conditions.…”