Practical Methodologies for the Synthesis of Indoles

Pd-Catalyzed α-Arylation of Sulfones in a Three-Component Synthesis of 3-[2-(Phenyl/methylsulfonyl)ethyl]indoles

“…1 For this reason, it is not surprising that since Fischer's pioneering indole synthesis in 1883, 2 numerous methodologies have been reported for the construction and functionalization of the indole skeleton. 3 Besides the vast array of more traditional reactions, recent advances in the area of transition metal-catalyzed transformations have led to the development of several new reliable methods for the synthesis of indoles from simple starting materials. 4 Among the variety of cross-coupling reactions, the palladium-catalyzed arylation of acidic C─H bonds 5 is of particular interest for the synthesis of this heteroaromatic compound from non-aromatic precursors.…”

“…Substituting the ligand for BINAP resulted, once again, in the formation of a complex reaction mixture (entry 3, Table 1). 3 : Tris(dibenzylideneacetone)dipalladium(0). Xantphos: 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene.…”

Crystal structure of 1-benzyl-3-((4-bromophenyl)amino)-4-(4-methoxyphenyl)-1H-pyrrole-2,5-dione, C24H19BrN2O3

“…Moreover, these multicomponent reactions (MCRs) provide facile access to complex products with high iterative efficiency potential [4], for the design of novel drug scaffolds from commercially available starting materials. We previously reported the use of this strategy to achieve the construction of various heterocyclic systems, including benzodiazepines [5], benzimidazoles [6], pyrazoles [7] and quinoxalines [8], as well as several other systems.…”

2-tert-Butyl-5,6,7,8,9,10-hexahydrocyclohepta[b]indole

“…Abstract: 2-tert- 6,7,8,9,indole was synthesized by reaction of cycloheptanone and (4-tert-butylphenyl)hydrazine hydrochloride in the presence of sodium acetate and sulfuric acid in glacial acetic acid via Fischer indole synthesis. .…”

“…The synthesis of 2 was accomplished by a straightforward Fischer indole synthesis [8,9] protocol from cycloheptanone (3) and (4-tert-butylphenyl)hydrazine hydrochloride (4).…”