Oxidative Transformation of 2-Furylanilines into Indolin-3-ones.

Oxidation of 2-furylaninlies with m-CPBA followed by treatment with a base provides access to functionalized indolin-3-ones. The designed oxidative transformation utilizes an underassessed chemical behavior of furyl-containing amines to form a C-N bond via engaging a ß-carbon atom of the furan core upon a ring-forming step, thereby providing an alternative disconnection toward nitrogen-containing heterocycles.

Interrupted Furan-Yne Cyclization: Access to Unsaturated Dicarbonyl Compounds and Their Subsequent Transformation into Functionalized Pyridazines.

The key carbenoid intermediate of transition-metal-catalyzed furan-yne cyclization in Hashmi phenol synthesis could be efficiently intercepted with water under the developed reaction conditions in order to provide access to functionalized unsaturated dicarbonyl compounds that might serve as convenient precursors for the straightforward synthesis of annulated pyridazines.

Acid-Catalyzed Cascade Reaction of 2-Alkylfurans with α,ß-Unsaturated Ketones: A Shortcut to 2,3,5-Trisubstituted Furans.

The convergent one-pot method toward trisubstituted furans has been developed. The key transformation behind the synthetic protocol comprises the cascade acid-catalyzed conjugated addition of furans to commercially available or easily accessible α,ß-unsaturated ketones followed by the rearrangement of the intermediate Michael adducts into isomeric furans. The prospect of utilizing the target products as building blocks for the preparation of potential functional molecules for organic electronics has been demonstrated.

Synthesis of (Het)aryl 2-(2-hydroxyaryl)cyclopropyl Ketones.

A simple general method for the synthesis of 1-acyl-2-(ortho-hydroxyaryl)cyclopropanes, which belong to the donor-acceptor cyclopropane family, has been developed. This method, based on the Corey-Chaykovsky cyclopropanation of 2-hydroxychalcones, allows for the preparation of a large diversity of hydroxy-substituted cyclopropanes, which can serve as promising building blocks for the synthesis of various bioactive compounds.

Intramolecular azavinyl carbene-triggered rearrangement of furans.

An intramolecular rhodium-catalyzed reaction of 1-tosyl-1,2,3-triazoles with furans has been explored. The tosylimino functionality was found to play a significant chemical role participating in the subsequent domino-transformations of a key reaction intermediate. One of the reaction pathways leads to valuable 2-formyl- and 2-acetylpyridine building blocks, which could be obtained in one-pot starting from easily accessible (furan-2-ylmethyl)propargyl amines. An original method for the synthesis of highly functionalized indolizines from the obtained pyridines has been proposed.

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,ß-unsaturated carbonyl moiety of the obtained compounds allows for accessing various heteroaromatic scaffolds through simple synthetic procedures.

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.