Electron-Transfer-Mediated Synthesis of Phenanthridines by Intramolecular Arylation of Anions from N-(ortho-Halobenzyl)arylamines: Regiochemical and Mechanistic Analysis
摘要:
The synthesis of a series of substituted phenanthridines by photostimulated C-C cyclization of anions from N-(ortho-halobenzyl)arylamines has been found to proceed in very good to excellent yields (79-95%) in liquid ammonia and in DMSO. The N-(ortho-halobenzyl)arylamines are obtained in good to very good isolated yields (44-85%) by nucleophilic substitution of ortho-halobenzylchlorides with different arylamines. The reaction of the anions of a diverse set of N-(ortho-halobenzyl)arylamines was studied, and the methodology was extended to the synthesis of tri-spheridine, a natural product, in very good yield. In order to explain the regiochemical outcome or these reactions, a theoretical analysis was performed with DFT methods and the B3LYP functional.
Selective Synthesis of Either Isoindole- or Isoindoline-1-carboxylic Acid Esters by Pd(0)-Catalyzed Enolate Arylation
摘要:
Two efficient palladium-catalyzed intramolecular alpha-arylation reactions of alpha-amino acid esters have been developed that allow either 1-isoindolecarboxylic acid esters or the corresponding isoindolines to be selectively synthesized simply by a slight change of reaction conditions.
A new strategy for the synthesis of tetrahydroisoquinolines based on the Pd0‐catalyzed intramolecular α‐arylation of sulfones is reported. The combination of this Pd‐catalyzed reaction with intermolecular Michael and aza‐Michael reactions allows the development of two‐ and three‐step domino processes to synthesize diversely functionalized scaffolds from readily available starting materials.
Isoindolines are synthesized by palladium-catalyzed coupling reaction of N-(2-iodobenzyl) anilines with α,β-unsaturated N-tosylhydrazones. The reaction has several potential advantages: (1) toleration of a wide range of functional groups, (2) easy to handle and with mild conditions, (3) enriches the isoindoline family, (4) two new bonds form in one step.
Cyanamides are an important class of molecules. This work describes a facile synthesis of disubstitutedcyanamides. Here, readily accessible 1-cyano-1, 2-benziodoxol-3-(1H)-one (CBX) was applied as a stable electrophilic cyanation reagent. Diverse secondaryamines were effectively cyanated. Moreover, secondary sulfonamides proved to be suitable substrates and were readily converted to N-alkyl(aryl
Supported-Pd catalyzed carbonylative synthesis of phthalimides and isoindolinones using Oxalic acid as in situ CO surrogate with 2-iodobenzamides and 2-iodobenzylanilines in ppm-level catalyst loading
作者:Shankar Ram、Pushkar Mehara、Ashish Kumar、Ajay Kumar Sharma、Arvind Singh Chauhan、Ajay Kumar、Pralay Das