A novel and efficient procedure for the synthesis of benzo[c]carbazoles has been achieved in moderate to high yields by the one-pot photochemical annulations of 2-chloroindole-3-carbaldehydes by styrenes via photodechlorination-initiated coupling of 2-chloroindole-3-carbaldehydes with styrenes, electrocyclic reactions and deformylative aromatization in the presence of pyridine.
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http://dx.doi.org/10.1039/b808854c | DOI Listing |
Acta Crystallogr E Crystallogr Commun
January 2025
Osaka Research Institute of Industrial Science and Technology, 1-6-50 Morinomiya, Joto-ku, Osaka 536-8553, Japan.
The asymmetric unit of the title compound is composed of one host mol-ecule, -4-(1 ,5 -3-aza-1,5(3,9)-dicarbazola-cyclo-octa-phane-3-yl)benzo-nitrile and one di-chloro-methane solvate mol-ecule, CHN·CHCl. The host mol-ecule possesses a planar chirality but crystallizes as a racemate in the space group 2/. It adopts an -configuration, in which two carbazole rings are partially overlapped with a parallel orientation.
View Article and Find Full Text PDFJ Org Chem
December 2024
Department of Chemistry, Faculty of Sciences, Atatürk University, 25240 Erzurum, Türkiye.
The synthesis of 5-aryl- or 5,6-diaryl-11-benzo[]carbazoles has been achieved from 3-styryl indoles through catalyst-free photoinitiated dehydrogenative cyclization transformation, providing a range of structurally diverse products in excellent yields under mild conditions. The protocol is also applicable to furan and thiophene samples. This Mallory-type reaction takes place in an argon atmosphere without external oxidants.
View Article and Find Full Text PDFSmall
January 2025
School of Materials Science and Engineering, Ocean University of China, Qingdao, 266100, China.
The 1H-benzo[f]indole (Bd[f]), a carbazole (Cz) isomer is first reported as the source of Cz-based phosphors in 2020. In this work, the novel carbazole isomers, 1H-benzo[g]indole (Bd[g]) based derivatives, are synthesized by a one-step solvent-free mechanical ball milling reaction, establishing a facile, efficient, and environmentally friendly method for the synthesis of new Cz isomer phosphorescent derivatives with high yields compared to previously reported multi-step solvent-based thermochemical synthesis routes of Bd[f] derivatives with low yields. Six Bd[g] derivatives with different substituents, namely OCH-Bd, In-Bd, Bn-Bd, F-Bd, Cl-Bd, and Br-Bd, are synthesized, which exhibit distinctly different single-crystal structures and phosphorescent properties.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
College of Material Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou, 310012, P. R. China.
We report herein a series of macrocycles in which the densely π-stacked charge-transfer (CT) donor/acceptor with naphthalenediimides (NDIs) or perylene diimide (PDI) as acceptor moiety pairing various donor moieties are locked by covalent bond. The X-ray crystallography of C8BDT-NDI reveals a short intramolecular π-stacking distance around 3.4 Å and the existence of intermolecular donor/acceptor π-stacking (3.
View Article and Find Full Text PDFJ Org Chem
October 2024
Department of Chemistry and Biochemistry, Texas State University, 601 University Dr., San Marcos, Texas 78666, United States.
Herein, we describe a novel reaction between C-2-substituted indoles and 2-nitroacetophenones leading to a variety of indole-containing heterocyclic scaffolds. At 60 °C in AcOH with HSO as catalyst, C-2 aryl indoles give 3-(2-nitrovinyl)-indoles with high or geometric selectivity depending on the type of substrate utilized. These compounds undergo an electrocyclization process in a sealed vial in a microwave apparatus in DMF at 250 °C to give benzo[]carbazoles and naphtho[2,1-]carbazoles depending on whether the C-2 aromatic moiety is phenyl or naphthyl.
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