The Chemistry of Phenanthridine and its Derivatives.

Synthesis of 6‐Substituted Phenanthridine Derivatives by Palladium‐Catalysed Domino Suzuki–Miyaura/Aza‐Michael Reactions

“…We found that the reaction of vinyl/aryl bromides and aryl boronates proceeded smoothly and to give the corresponding products 9 in good to excellent yields. For example, using vinyl bromides, under the optimized conditions, the desired compounds (i.e., 9a-9c, 9h, and 9i) were obtained in good yields (Table 5, entries [1][2][3][8][9]. Heteroaryl substrates were also suitable coupling partners, and gave the corresponding products in satisfactory yields.…”

“…[1,2] Some 5,6-secolycorines, with a 5,6-dihydrophenanthridine skeleton, have been reported to act as potent inhibitors of acetylcholinesterase (AChE), [3] and a series of phenanthridinyl acetamides have been synthesized and evaluated as bradykinin B1 receptor antagonists, which are potentially useful in the prevention of inflammation. [4] To discover more biologically active compounds, a facile and highyielding route to construct the 6-substituted phenanthridine framework is required.…”

“…To the best of our knowledge, there are few methods that could be used to prepare various 5,6-dihydrophenanthridine-6-acetate derivatives efficiently under simple and mild conditions in excellent yields in one pot. 1 Miyaura reaction followed by intramolecular aza-Michael addition. This method is applicable to the synthesis of a wide range of substituted phenanthridines from simple substrates.…”

Synthesis of benzo[c][1,8]phenanthrolin-6-one through cyclization ofN-(isoquinol-5-yl)-2-bromo-benzamide derivatives

“…The phenanthridine nucleus is found in a variety of natural alkaloids as well as in synthetic compounds of biological importance [1][2][3]. Since 1970, the benzo[c]-phenanthridine alkaloids have been the focus of interest for their biological effects such as their potential antitumor properties [4,5].…”

“…All these compounds are strong topoisomerase I inhibitors. With the aim of synthesizing new antitumoral compounds, we attempted to replace the benzo[c]phenanthridine ring system by a benzo[c] [1,8]phenanthroline [19]. We report in this paper our results on the synthesis of the benzo[c] [1,8]phenanthrolin-6-one 3 via the key cyclization of N-(isoquinol-5-yl)-2-bromo-4,5-dimethoxybenzamide (4) either using the Kessar benzyne cyclization [20,21] or a palladium-assisted intramolecular biaryl coupling reaction [22].…”