Synthesis of N-acyl carbazoles, phenoxazines and acridines from cyclic diaryliodonium salts

• Nils Clamor,
• Mattis Damrath,
• Thomas J. Kuczmera,
• Daniel Duvinage and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2024, 20, 12–16, doi:10.3762/bjoc.20.2

• tested this method with a wide range of amides and iodonium triflates, proving its versatility with numerous substrates. Beyond carbazoles, we also produced a variety of other N-heterocycles, such as acridines, phenoxazines, or phenazines, showcasing the robustness of our technique. In a broader sense

Unravelling a trichloroacetic acid-catalyzed cascade access to benzo[f]chromeno[2,3-h]quinoxalinoporphyrins

• Chandra Sekhar Tekuri,
• Pargat Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2023, 19, 1216–1224, doi:10.3762/bjoc.19.89

• microbial strains [16][17]. Thorough literature search revealed that the fused heterocycles such as benzo[a]pyrano[2,3-c]phenazines and benzo[a]chromeno[2,3-c]phenazines have been prepared as fluorescent materials [18][19]. On the other hand, xanthenes exhibited a number of biological and pharmaceutical

Mutational analysis of a phenazine biosynthetic gene cluster in Streptomyces anulatus 9663

• Orwah Saleh,
• Katrin Flinspach,
• Lucia Westrich,
• Andreas Kulik,
• Bertolt Gust,
• Hans-Peter Fiedler and
• Lutz Heide

Beilstein J. Org. Chem. 2012, 8, 501–513, doi:10.3762/bjoc.8.57

• , 72076 Tübingen, Germany 10.3762/bjoc.8.57 Abstract The biosynthetic gene cluster for endophenazines, i.e., prenylated phenazines from Streptomyces anulatus 9663, was heterologously expressed in several engineered host strains derived from Streptomyces coelicolor M145. The highest production levels were

• obtained in strain M512. Mutations in the rpoB and rpsL genes of the host, which result in increased production of other secondary metabolites, had no beneficial effect on the production of phenazines. The heterologous expression strains produced, besides the known phenazine compounds, a new prenylated

• antiparasitic activities, and as inhibitors of angiotensin converting enzyme (ACE) or testosterone-5-α-reductase [1]. The synthetic phenazine clofazimine has been approved for human therapy in the treatment of leprosy. Some of the other naturally occurring phenazines are bacterial virulence factors [1]. Natural

Syntheses and properties of thienyl-substituted dithienophenazines

• Annemarie Meyer,
• Eva Sigmund,
• Friedhelm Luppertz,
• Gregor Schnakenburg,
• Immanuel Gadaczek,
• Thomas Bredow,
• Stefan-S. Jester and
• Sigurd Höger

Beilstein J. Org. Chem. 2010, 6, 1180–1187, doi:10.3762/bjoc.6.135

• : oligothiophenes; phenazines; scanning tunneling microscopy; self-assembled monolayers; TD-DFT calculations; Introduction Thiophene based oligomers and polymers have drawn considerable interest as active materials in various fields of organic electronics such as organic light-emitting diodes (OLEDs), organic thin

• well as cyclic and polycyclic thiophenes are valuable templates for the epitaxial coadsorption of adlayers, in particular for fullerenes and metallacycles [14][15][16][17]. Results and Discussion Here we report the syntheses of two isomeric benzodithiophenediones, their respective phenazines and their

• diketones 4 and 8 with diaminobenzenes 9a and 9b, containing methyl and hexyl side groups [25], in pure acetic acid at 50 °C gave the phenazines 10 and 11 as yellow solids in 50–93% yield (Scheme 3) [26]. The hexyl derivatives 10b and 11b showed a significantly higher solubility than the methyl analogues