Published data of the last 10 years concerning development new and upgrading known approaches to indole synthesis are integrated analyzed. Modern versions classical syntheses such as Fischer synthesis, Nenitzescu Ullmann reaction, Leimgruber – Batcho Reissert Bartoli Madelung Cadogan Sundberg reaction considered. The presented include transformations heterocycles, from o -alkynylanilines, reductive cyclization nitrobenzene derivatives, with use arynes catalysis by N-heterocyclic carbenes....

The N-(2-pyridyl)-N'-ethylpiperazines are important structural motifs in several medicinally relevant compounds. Known synthetic methods toward these structures multistep and generally based on the SNAr-chemistry; their applicability is significantly limited to substrates containing electron-withdrawing groups. Here, we describe a new methodology for rapid modular access this privileged scaffold. Importantly, developed protocol proved be very general efficient substituents of different...

Employing DABCO as a substrate, aryl(mesityl)iodonium triflates are introduced arylating agents for tertiary sp3-nitrogen. Mild conditions and exceptional selectivity of the aryl group transfer allow unprecedented N-aryl-DABCO salts to be obtained, bearing substituents different electronic natures. This metal-free methodology has no analogy among known transition-metal-based reactions. The utility isolated is demonstrated preparation flibanserin.

The visible-light-induced arylation of tertiary phosphines with aryl(mesityl)iodonium triflates to produce the quaternary phosphonium salts occurs under mild, metal, and catalyst-free conditions. Photo-excited EDA complexes between diaryliodonium supposedly enable this transformation, which is difficult achieve through traditional ground-state reactions. Demonstrating high functional group tolerance, broad scope, complete selectivity aryl transfer, method particularly compatible sterically...

A variety of N-alkylated and N-arylated derivatives methyl 1H-indole-3-carboxylate were synthesized efficiently via Ullmann-type intramolecular arylamination, using the CuI−K3PO4−DMF system. This catalytic amination procedure can be performed with good to high yields under mild conditions an air atmosphere.

Abstract A simple route to various N ‐substituted 1‐amino‐1 H ‐indole‐3‐carboxylates by use of copper(I)‐catalyzed intramolecular ‐arylation has been established. For the preparation ‐monosubstituted and ‐unsubstituted derivatives, cyclization Boc‐protected enehydrazines subsequent deprotection were applied. Furthermore, 1‐alkoxyindole‐3‐carboxylates can be synthesized same protocol(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

The reactions of pyridine-N-oxides with Ph3P under the developed conditions provide an unprecedented route to (pyridine-2-yl)phosphonium salts. Upon activation DABCO, these salts readily serve as functionalized 2-pyridyl nucleophile equivalents. This umpolung strategy allows for selective C2 functionalization pyridine ring electrophiles, avoiding generation and use unstable organometallic reagents. protocol operates at ambient temperature tolerates sensitive functional groups, enabling...

A new protocol for the preparation of N-substituted indole-3-carboxylates has been developed. The key C–N bond formation occurs under transition-metal-free conditions employing a t-BuOK/DMF system without special initiators or additives. Across number substrates, indoles were afforded in yields higher comparable to those obtained transition-metal-catalyzed conditions. While demonstrating high functional group tolerance, are particularly attractive manufacturing halogenated that cannot be...

Arylation methods based on the generation and use of aryl radicals have been a rapidly growing field research in recent years currently represent powerful strategy for carbon – heteroatom bond formation. The progress this is related to advances radicals. used radical precursors include halides, aryldiazonium diaryliodonium salts, arylcarboxylic acids their derivatives, arylboronic acids, arylhydrazines, organosulfur(II, VI) compounds some other compounds. Aryl are generated under mild...

Readily accessible o-bromobenzylketones and primary alkyl amines anilines were used for the construction of substituted indoles in good to excellent yields. The sequence involves a titanium-mediated reaction ketones with afford imines subsequent intramolecular cyclization into employing copper catalysis. two-step protocol allows preparation bearing both N-alkyl N-aryl groups as well N-unsubstituted without isolation intermediates is tolerant wide range functionality.

Methods for the synthesis of polyfluoro(chloro, bromo) derivatives C60 fullerene and their structures are described. The reactivity these compounds is demonstrated considering redox reactions, nucleophilic substitution, radical addition, cycloaddition electrophilic arylation.

Abstract A one‐pot Sonogashira cross‐coupling/5‐ endo ‐ dig cyclization procedure leading to 2‐aryl‐4,5,6,7‐tetrahydroindoles was developed. This short (only two steps from commercially available compounds) sequence avoids harsh conditions and expensive catalysts. Our is highly tolerant a range of functional groups (amino, nitro, carboxy, cyano, hydroxy, bromo). family 21 tetrahydroindoles synthesized on gram scale in good excellent yields, which indicative the general character scalability...

We have developed an efficient and stereoselective route to trans-fused octahydrocyclohepta[b]pyrrol-4(1H)-ones. The key features of our synthesis include the regioselective epoxide ring-opening alkynyl oxiranes a aza-Cope-Mannich reaction. target compounds were prepared in 3-6 steps from commercially available starting materials (61-75% overall yield) with minimal chromatographic purification. devised using Shi epoxidation or (R)-1-phenylethylamine as source chirality.

Abstract N ‐(Pyrid‐2‐yl)‐substituted azolium and pyridinium salts, precursors for hybrid NHC‐containing ligands, were obtained with excellent regioselectivity, employing a deoxygenative CH‐functionalization of pyridine‐ ‐oxides substituted imidazoles, thiazoles, pyridine. Unlike the traditional S Ar‐based methods, this approach provides high yields substrates bearing substituents different electronic nature. The utility salts thus prepared was also highlighted by synthesis...