TBAF-assisted N-arylation and benzylation of benzazoles such as 1H-benzimidazole, 1H-indole, and 1H-benzotriazole with aryl and benzyl halides have been demonstrated under the ligand/base/solvent-free conditions. In the presence of CuBr2 and TBAF (n-Bu4NF), the azoles underwent N-arylation and benzylation with aryl and benzyl halides smoothly in moderate to good yields. It is noteworthy that the reaction is conducted under the ligand/base/solvent-free conditions.
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http://dx.doi.org/10.1021/jo900752z | DOI Listing |
Org Biomol Chem
January 2024
Institut für Chemie, Technische Universität Chemnitz, Straße der Nationen 62, 09111 Chemnitz, Germany.
Two tandem catalytic systems are described for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts as starting materials. 4-Aryl-3-pyrrolyl- and 4-aryl-3-indolyl-maleimides were successfully obtained a Pd(OAc)/PPh based protocol. In contrast, maleimide-fused pyrrolo and indolo[1,2-]quinolines were obtained in a complementary methodology using CuI/L-proline.
View Article and Find Full Text PDFMolecules
September 2023
Department of Applied Chemistry, Global Center for Pharmaceutical Ingredient Materials, Kyung Hee University, Yongin-si 17104, Gyeonggi, Republic of Korea.
Inflammatory-related diseases are becoming increasingly prevalent, leading to a growing focus on the development of anti-inflammatory agents, with a particular emphasis on creating novel structural compounds. In this study, we present a highly efficient synthetic method for direct -arylation to produce a variety of (2)-arylindazol-3(2)-ones , which exhibit anti-inflammatory activity. The Chan-Evans-Lam (CEL) coupling of (1)-benzyl-indazol-3-(2)-ones with arylboronic acids in the presence of a copper complex provided the corresponding (2)-arylindazol-3(2)-ones in good-to-excellent yields, as identified with NMR, MS, and X-ray crystallography techniques.
View Article and Find Full Text PDFJ Org Chem
January 2021
Bioorganische Chemie, Institut für Chemie, Universität Hohenheim, Garbenstraße 30, Stuttgart D-70599, Germany.
A direct and operationally simple method for the regioselective synthesis of 2-aryl-substituted 2-indazoles is reported. The Pd-catalyzed reaction between easily available 2-bromobenzyl bromides and arylhydrazines employing CsCO as the base and -BuPHBF as the ligand in DMSO at 120 °C in a sealed tube delivers the 2-substituted-2-indazoles in a single synthetic step with yields up to 79%. The new method is based on a regioselective intermolecular -benzylation followed by intramolecular -arylation and oxidation.
View Article and Find Full Text PDFOrg Lett
April 2020
Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, Tamil Nadu, India.
Org Lett
July 2019
Center for Metareceptome Research, College of Pharmacy , Chung-Ang University, 84 Heukseok-ro, Dongjak , Seoul 06974 , Republic of Korea.
A tandem three-component reaction has been developed for the synthesis of spirocyclic 2-indolinylformamidines through a cooperative action of palladium and copper catalysts. The Pd-catalyzed benzylation of α-isocyano lactams with 2-bromobenzyl bromides allows efficient formation of α-substituted α-isocyano lactams. A subsequent Cu-catalyzed amine addition to the isocyanide moiety provides amidine intermediates that readily undergo intramolecular N-arylation via the cooperative action of Pd/Cu catalysis, allowing a facile chiral resolution of the spirocyclic 2-indolines.
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