Yurii V. Shklyaev

Synthesis of 1-functionalized di- and tetramethyl-3,4-dihydrobenzofuro[3,2-g]-and [2,3-h]isoquinoline derivatives

Linear and angular 1-substituted derivatives of 3,3-di- and 3,3,4,4-tetramethyl-3,4-dihydrobenzofuroisoquinoline were obtained under Ritter reaction conditions, and the stereochemical features of these compounds were analyzed.

Synthesis of new pyrrolo[3,2-l]acridinones and pyrrolo[3,2-c][1,8]naphthyridinones by condensation of methoxybenzenes or phenols with isobutyric aldehyde and o-aminonitriles

A reaction of methoxybenzenes or phenols with isobutyric aldehyde and 2-amino-5-nitro- or 2-amino-4-chlorobenzonitriles in concentrated H2SO4 medium was used for the preparation of new pyrrolo[3,2-l]acridinone derivatives. Analogous reactions using 2-amino-3-pyridinecarbonitrile enabled the synthesis of previously unknown benzo[b]pyrrolo[3,2-c][1,8]naphthyridinones.

Direct heterocyclization of (3,4-dihydroisoquinolin-1(2 H)- ylidene)acetamides with aroylketenes. Crystal and molecular structure of (Z)-3-(4a-methyl-1,3,4,4a,5,10b- hexahydrophenanthridin-6(2 H)-ylidene)-4-phenylpyridine- 2,6(1 H,3 H)-dione

Aroylketenes generated by thermolysis of 6-aryl-2,2-dimethyl-4H-1,3-dioxin-4-ones react with ( Z)-2-[3,3-dimethyl-3,4-dihydroisoquinolin-1(2 H)-ylidene]acetamides and (Z)-2-[4amethyl-1,3,4,4a,5,10b-hexahydrophenanthridin-6(2 H)-ylidene]acetamide to produce (Z)-4aryl-3-(3,3-dimethyl-3,4-dihydroisoquinolin-1(2 H)-ylidene)pyridine-2,6(1 H,3 H)-diones and (Z)-3-(4a-methyl-1,3,4,4a,5,10b-hexahydrophenanthridin-6(2 H)-ylidene)-4-phenylpyridine2,6(1 H,3 H)-dione. The crystal and molecular structure of ( Z)-3-(4a-methyl-1,3,4,4a,5,10bhexahydrophenanthridin-6(2 H)-ylidene)-4-phenylpyridine-2,6(1 H,3 H)-dione was confirmed by X-ray analysis.

Design of Multi-Component Reactions

Multi-component reactions (MCRs) have now been well established as a powerful synthetic tool for creating molecular complexity and diversity and are undoubtedly well suited for the drug discovery program. Another potential that has probably received less attention among synthetic chemists is the opportunity offered by MCRs for the development of new fundamentally important transformations (reactions). Indeed, although an MCR is composed of a series of known bimolecular reactions, the overall transformation could be novel. Consequently, it provides chemists the opportunities to uncover transformations that were otherwise difficult to realize. In this talk, we will present our recent work in this field, including: (1) the oxidative homologation of aldehydes to amides, (2) the oxidative coupling of aldehydes and isocyanides to α-ketoamides, (3) oxidative isocyanide-based MCRs, and (4) the enantioselective Passerini reaction.

Novel Reagents for Multi-Component Reactions

Ketenimines are a class of versatile and highly reactive intermediates that can participate in a variety of organic reactions, such as nucleophilic additions, radical additions, [2 + 2] and [2 + 4] cycloadditions, and sigmatropic rearrangements. In this presentation, we report on a series of multi-component reactions that involve a ketenimine intermediate. These reactions could furnish diverse heterocyclic compounds, including functionalized iminocoumarin, iminodihydroqunolines, iminothiochromens, pyrrolines, isoquinolines, pyridines, β-lactams, imino-1,2-dihydrocoumarins, and benzimidazoles.