Efficient solid-phase synthesis of 2,3-substituted indoles

CC Bond‐Forming Reactions

“…If alkene and alkyne are tethered, tricyclic structures can be obtained. Thus, Kuboto et al reported the intramolecular Pauson-Khand reaction of DES-bound 2-3 di-dioxy 2,3-unsaturated propargyl glucoside (413). The latter were accessible from glucal via a Ferrier reaction.…”

“…Due to the fact that the indole nucleus is widely present in molecules that interact with G-protein-coupled receptors (GPCRs), researchers at Bristol-Myers Squibb have investigated a solid-phase version of the modified Madelung indole synthesis [413]. After immobilizing o-cyanomethylaniline (601) on Bal resin through a twostep reductive amination, subsequent acylations of the supported aniline were performed with a variety of substituted benzoyl (602), heteroaroyl, and aliphatic acid chlorides.…”

Synthetic approaches towards indoles on solid phase recent advances and future directions

“…Wacker and Kasireddy 20 have utilised the modified Madelung indole synthesis successfully on solid phase. 2,3-Disubstituted indoles were obtained in excellent yields and purities.…”

Recent Advances in the Synthesis of N-Containing Heteroaromatics via Heterogeneously Transition Metal Catalysed Cross-Coupling Reactions

“…The rich structural diversity encountered in these compounds, in addition to their biological and pharmaceutical relevance, have motivated more than 100 years of research aiming at developing economical, efficient and selective synthetic strategies for these compounds [ 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 ]. For example, as far as indoles are concerned, these methodologies include the Fisher synthesis from aryl hydrazones [ 9 , 14 ], the Batcho-Limgruber synthesis from o -nitrotoluenes and dimethylformamide acetals [ 15 ], the Gassman synthesis from N- haloanilines [ 16 , 17 ] or the Madelung cyclisation of N -acyl- o -toluidines [ 18 ]. For quinolones, a less developed area, the most remarkable methodologies include the condensation of anilines with β-ketoesters followed by cyclisation [ 10 , 11 , 12 ] or the heterocyclisation of 2-aminochalcones [ 13 ].…”