Satenik Mkrtchyan

Synthesis of Fluorinated Purine and 1-Deazapurine Glycosides as Potential Inhibitors of Adenosine Deaminase

The synthesis of 2- and 6-trifluoromethylated purines and 1-deazapurines was performed by formal [3 + 3]-cyclization reactions of 5-aminoimidazoles with a set of trifluoromethyl-substituted 1,3-CCC- and 1,3-CNC-dielectrophiles. The corresponding fluorinated nucleosides were synthesized by glycosylation of 9-unsubstituted purines and 1-deazapurines with peracetylated β-ribose, β-glucose, and rhamnose and subsequent deprotection. These scaffolds can be considered as potential inhibitors of adenosine deaminase (ADA) and inosine monophosphate dehydrogenase (IMPDH) enzymes.

Transition-Metal-Catalyzed Arylation of Nitroimidazoles and Further Transformations of Manipulable Nitro Group

Pd- or Ni-catalyzed C-H arylation of 4-nitroimidazole derivatives directed by a manipulable nitro group was developed. The reaction tolerates a wide range of substituted aryl halides and 4-nitroimidazoles. The experiments indicated that the nitro group has influence on regioselectivity of the reaction. In addition, we have shown that the efficiency of the Suzuki-Miyaura cross-coupling reaction of nitroimidazoles is slightly lower in comparison to the direct C-H arylation. The exploration of the chemical potential of the nitro group and a putative reaction mechanism are discussed.

Chelation control in the [3 + 3] annulation reaction of alkoxy-substituted 1,1-diacylcyclopropanes with 1,3-bis(trimethylsilyloxy)-1,3-butadienes. diversity-oriented synthesis of isochromanes.

Functionalized arenes were prepared by chelation-controlled [3 + 3] cyclization/cyclopropane opening reactions of 1-trimethylsilyloxy-1,3-butadienes with benzyloxy- or methoxy-substituted 1,1-diacylcyclopropanes. A number of benzyloxy-substituted derivatives were transformed into isochromanes by deprotection and subsequent cyclization. Mixed chromanes-isochromanes were prepared starting with 1,3-bis(silyloxy)-1,3-butadienes containing a remote chloride group.

Regioselective Direct Arylation of Fused 3-Nitropyridines and Other Nitro-Substituted Heteroarenes: The Multipurpose Nature of the Nitro Group as a Directing Group

We report Pd‐ and Ni‐catalysed, guided and regioselective CH arylations of a series of fused 3‐nitropyridines. The method described here is a facile tool for the chemical functionalisation of drug‐like fused pyridines. The scope and limitations of the reaction, the chemical potential of the nitro group and a putative reaction mechanism are discussed.

Synthesis of 4-quinolones, benzopyran derivatives and other fused systems based on the domino ANRORC reactions of (ortho-fluoro)-3-benzoylchromones

Herein we reported a transition metal free strategy for the synthesis of 4-quinolones, benzopyran derivatives and other fused systems by the domino reaction of 3-benzoyl-chromones, containing a leaving group in the position-2 of the benzoyl moiety, with aliphatic amines, anilines and different binucleophiles. The developed strategy is suitable for a broad range of substrates, namely according to the applied nucleophile the reaction provides different final products with excellent chemoselectivity. The mechanistic studies resulted in the detection and isolation of several intermediates.

Tandem dinucleophilic cyclization of cyclohexane-1,3-diones with pyridinium salts

Summary The cyclization of cyclohexane-1,3-diones with various substituted pyridinium salts afforded functionalized 8-oxa-10-aza-tricyclo[7.3.1.02,7]trideca-2(7),11-dienes. The reaction proceeds by regioselective attack of the central carbon atom of the 1,3-dicarbonyl unit to 4-position of the pyridinium salt and subsequent cyclization by base-assisted proton migration and nucleophilic addition of the oxygen atom to the 2-position, as was elucidated by DFT computations. Fairly extensive screening of bases and additives revealed that the presence of potassium cations is essential for formation of the product.