Maxim G. Uchuskin

A Simple Route to Polysubstituted Indoles Exploiting Azide Induced Furan Ring Opening

A straightforward, efficient indole synthesis based on thermolysis of 2-(2-azidobenzyl)furans with attack of the formed nitrene moiety onto the ipso position of furan ring has been developed. The cyclization is accompanied by furan ring opening and affords indoles with a 2-acylvinyl substituent suitable for further modifications.

Oxidative Furan-to-Indole Rearrangement. Synthesis of 2‑(2- Acylvinyl)indoles and Flinderole C Analogues

Oxidative rearrangement of 2-(2-aminobenzyl)furans affording 2-(2-acylvinyl)indoles in a stereocontrolled manner in good-to-excellent yields has been developed. Thus, (2-aminobenzyl)furans with electron-releasing alkoxy substituents in the phenyl group form only E-isomers of 2-(2-acylvinyl)indoles. Conversely, substrates without such substituents produce target products as Z-isomers exclusively. A short diastereoselective method for the transformation of the obtained 2-(2-acylvinyl)indoles into antimalarial bisindole alkaloid flinderole A-C analogues has been developed.

Simple and Convenient Synthesis of 4-Unsubstituted-3- (3-Oxoalkyl)isocoumarins

Abstract A simple transformation of 2‐alkylfurans and 2‐formylbenzoic acids into 4‐unsubstituted 3‐(3‐oxoalkyl)isocoumarins is described. It is based on the synthesis of 2‐(2‐carboxybenzyl)furans followed by their acid‐catalyzed recyclization to the target isocoumarins.

A simple method for the synthesis of furfuryl ketones and furylacetic acid derivatives

A simple preparative method has been developed for the synthesis of aryl(furfuryl) ketones, amides, and furylacetic acid esters, based on radical alkylation of furan derivatives at the α-position with О-ethyl(phenacyl)xanthogenates and phenacyl iodides in the presence of Fentons reagent (H2O2/FeSO4 · 7H2O) in DMSO. The range of applicability and mechanisms for the formation of major and side products have been considered.

Catalytic Alkylation of Furans by π-Activated Alcohols (Review)

Progress in the field of catalytic alkylation of furans by π-activated alcohols over the last 15 years is reviewed. The occurence of benzyl-, allyl-, and propargylfurans in natural sources and their biological activity is also discussed.

Intramolecular Palladium-Catalyzed Oxidative Amination of Furans: Synthesis of Functionalized Indoles

Unconventional modification of palladium-catalyzed oxidative amination where a furan ring serves as a masked olefin is described. The designed chemical process provides 2-(2-acylvinyl)indole derivatives with up to a 93% yield and excellent E-selectivity. A highly reactive α,β-unsaturated carbonyl moiety of the obtained compounds allows for accessing various heteroaromatic scaffolds through simple synthetic procedures.

A General Synthetic Route to Isomeric Pyrrolo[1,2-x][1,4]diazepinones

A simple one-pot method for the synthesis of isomeric pyrrolo[1,2- x][1,4]diazepinones in reasonable yields was developed. The method is based on the condensation of readily available N-Boc amino acids with biomass-derived furans containing aminoalkyl groups followed by deprotection, furan ring opening, and Paal-Knorr cyclization. Using this approach, we synthesized pyrrolo[1,2- a][1,4]diazepin-3(2 H)-ones from furfurylamines and β-amino acids and pyrrolo[1,2- d][1,4]diazepin-4(5 H)-ones from 2-(2-furyl)ethylamines and α-amino acids. The cytotoxicity of the synthesized pyrrolodiazepinones was studied.

Copper(II) bromide-catalyzed conjugate addition of furans to α,β-unsaturated carbonyl compounds

A simple method for the synthesis of 2-(3-oxoalkyl)furan derivatives based on conjugate addition of 2-substituted furans to various α,β-unsaturated carbonyl compounds in the presence of copper(II) bromide as catalyst was developed.

Synthesis of quinolines via acid-catalyzed cyclodehydration of 2-(tosylamino)chalcones

The acid-catalyzed cyclodehydration of (E)-3-[(2-tosylamino)phenyl]-1-(het)arylprop-2-en-1-ones to 2-substituted quinolones was investigated. The reaction proceeds via the key step of (E,Z)-isomerization with subsequent intramolecular cyclization affording the target compounds in high yields.