Ueber eine neue Synthese der Phenanthridinbasen

Abstract

1182214. Am6 P i c t e t und A. Hubert: Ueber eine neue Syntheee der Phenanthridinbesen. (Eingegangen a m 11. April; mitgetheilt in der Sitzung von Hrn. S. Gabriel.)Zur Darstellung der Basen der Phenanthridinreihe sind bis jetzt zwei synthetische Methoden bekannt gegehen worden. Erstere berubt auf der pyrogenen Condensation der Benzylidenverbindungen der primiiren aromatischen Amine. So wurden das Pbenanthridin selbst aus Anilin l ) , zwei in einem der Benzolkerne methylirte Phenanthridine aus 0-und p-Toluidin und die beiden Chrysidine aus a-und /i-Naphtylamin ') gew onnen. R Rso werden die ieomeren Acyl-o-aminobiphenyle in Phenanthridine iibergefiihrt: / / ' '~ 1) P i c t e t u. A n k e r s m i t , diese Berichte 28, 3339 u. Ann. d. Chem. 4 P i c t e t und E r l i c h , Ann. d. Chem. 266, 153. 3) Ann. d. Chem. 276, 250. 266, 138.

Total Syntheses of Lactonamycin and Lactonamycin Z with Late‐Stage A‐Ring Formation and Glycosylation

“…The Bischler–Napieralski reaction was originally reported in 1893 as a method for synthesizing 3,4‐dihydroisoquinolines from N ‐acetyl phenethylamines in the presence of P 2 O 5 9. Three years later, Pictet and Hubert applied this reaction to the synthesis of phenanthridinone from 2‐ethoxycarbonylaminobiphenyl using zinc chloride 10a. 100 years of continuous improvements has made this series of Friedel–Crafts‐type cyclizations useful for the construction of dihydroisoquinolinones 10b–h.…”

Copper(0)/Selectfluor System-Catalyzed Tandem Annulation/Aromatization ofo-Aryl Benzenesulfonylimides:A Facile Synthesis of 6H-Phenanthridines

“…Based on the above experiments and previous literature, [11,13,14] a possible mechanism for the Cu(0)/Selectfluor system-catalyzed annulation/aromatization of 1a is proposed in Scheme 3. First, the redox reaction between Cu(0) and Selectfluor may produce a copper species FCuBF 4 (5) and release base 6. [11a] With the aid of 6, 5 may be transferred into copper species XCuOH (X＝F or BF 4 , 7) in the presence of water.…”

“…[2] Several representative and biologically active compounds contain-ing 6H-phenanthridine scaffold are presented in Figure 1. To date, numerous methods have been established for the construction of 6-substituted phenanthridines [4～8] involving the classic Pictet-Hubert condensation, [5] metal-catalyzed cross-coupling/cyclization, [6] radical-mediated cyclization of ortho-substituted biphenyls, [4,7] and others. [8] In contrast, efficient and convenient methods for the preparation of 6H-phenanthridines have been relatively underexplored.…”

Synthesis of Phenanthridinone Derivatives by Direct Arylation. Characterization of the Absorption and Emission Spectra for Representative Examples

“…15 Outros métodos empregam derivados de bifenila substituídos na posição 2, por exemplo a reação de Pictet-Hubert 16 e a sua modificação de MorganWalls, 17 aplicada à síntese de fenantridinas seguida por oxidação, 18 ou a ciclização do etil carbamato de 2-aminobifenila, 19 e a reação de 2-aminobifenila com fosgênio (Figura 2, E), 20 ou a sequência de reações envolvendo a nitração, redução e desidratação aplicada ao ácido bifenil-2-carboxílico, 21 e a oxidação de bifenil-2-carboxamidas (Figura 2, D). 22 Além destes métodos, as fenantridinonas (1) podem ser obtidas pelo rearranjo térmico de 2-alcoxifenantridinas 23 ou cicloadições de Diels-Alder, 24 ou, fotoquimicamente, por irradiação de aril-hidrazonas de benzotriazol (Figura 2, B), 25 ou por foto-desidro--halogenação de benzoilanilinas (Figura 2, C), [26][27][28] foto-ciclo-adição de estirenos com isoquinolinonas, 29 ou por pirólise de derivados de 3-arilidenoamino-1,2,3-benzotriazin-4-onas 30 e de benzoilbenzotriazóis (Figura 2, B).…”