Firuza M. Shakirova

Bio: Firuza M. Shakirova is an academic researcher from Saint Petersburg State University. The author has contributed to research in topics: Deep eutectic solvent & Eutectic system. The author has an hindex of 3, co-authored 6 publications receiving 52 citations.

Fe(II)/Au(I) Relay Catalyzed Propargylisoxazole to Pyridine Isomerization: Access to 6-Halonicotinates.

Abstract: An efficient synthesis of methyl nicotinates/6-halonicotinates by the domino isomerization of 4-propargyl/(3-halopropargyl)-5-methoxyisoxazoles under Fe(II)/Au(I) relay catalysis was developed. It was found that FeNTf2 is an effective catalyst for first step of the domino isomerization, transformation of isoxazole to 2H-azirine, which is compatible with Ph3PAuNTf2, catalyzing the second step.

Isoxazole Strategy for the Synthesis of 2,2′-Bipyridine Ligands: Symmetrical and Unsymmetrical 6,6′-Binicotinates, 2,2′-Bipyridine-5-carboxylates, and Their Metal Complexes

Abstract: An effective strategy was developed for the synthesis of new 2,2′-bipyridine ligands, symmetrical and unsymmetrical 6,6′-binicotinates, and 2,2′-bipyridine-5-carboxylates, from 4-propargylisoxazoles. The synthesis of symmetrical 2,2′-disubstituted 6,6′-binicotinates was achieved using the Eglinton reaction of 5-methoxy-4-(prop-2-yn-1-yl)isoxazoles with Cu(OAc)2, followed by Fe(NTf2)2/Au(NTf2)tBuXPhos-catalyzed isomerization of the so-formed mixture of isoxazole/azirine-substituted biacetylenic intermediates. Unsymmetrical 2,2′-disubstituted 6,6′-binicotinates were prepared via a copper-free Sonogashira coupling of 5-methoxy-4-(prop-2-yn-1-yl)isoxazoles with 6-bromonicotinates to give methyl 6-(3-(5-methoxyisoxazol-4-yl)prop-1-ynyl)pyridine-3-carboxylates, followed by a transformation of the propargylisoxazole moiety of the adduct into the pyridine fragment under Fe(II)/Au(I) relay catalysis conditions. 6-(Pyrid-2-yl)nicotinates were synthesized by a Stille-type coupling of 2-(tributylstannyl)pyridine with...

A synergistic effect of hydrophobic deep eutectic solvents based on terpenoids and carboxylic acids for tetracycline microextraction.

Abstract: Hydrophobic deep eutectic solvents were investigated for tetracycline microextraction. It was found that a deep eutectic solvent consisting of thymol and octanoic acid provided a synergistic effect on tetracycline extraction. In this paper, a novel liquid–liquid microextraction procedure for the HPLC-DAD determination of tetracyclines in milk samples was proposed.

Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes

Abstract: This review describes the gold-catalyzed reactions of specially activated alkynes, allenes, and alkenes. Such species are characterized by the presence of either electron-donating or electron-withdrawing groups as substituents of the carbon π-system. They are intrinsically polarized, and when compared to their nonspecially activated counterparts can therefore be involved in gold-catalyzed transformations featuring increased regio-, stereo-, and chemoselectivities. The chemistry of specially activated carbon π-systems under homogeneous gold catalysis is extremely rich and varied. The reactivity observed with nonspecially activated unsaturated systems can often be transposed to specially activated ones without loss of efficiency. However, specially activated carbon π-systems also exhibit specific reactivities that cannot be attained with regular substrates. In this family of carbon π-systems, ynamides and their analogs, along with alkynyl carbonyl derivatives, are the classes of substrates that have retained the most attention. This review provides an overview of the chemistry developed with all classes of specially activated carbon π-systems by discussing their general and specific reactivities, presenting and commenting on their gold-catalyzed transformations as well as their applications.

Gold-catalyzed heterocyclic syntheses through α-imino gold carbene complexes as intermediates

Abstract: Gold carbene complexes have been recognized as common intermediates in gold-catalyzed organic syntheses. In this field, α-imino gold carbene complexes, in the last few years, have emerged as valuable intermediates toward the synthesis of N-heterocycles. This review is dedicated toward formulating a comprehensive compilation of the different methodologies for heterocyclic synthesis, postulating the participation of α-imino gold carbene complexes as intermediates. In addition to the scarce examples involving the direct formation of α-imino diazo compounds from gold decomposition, the use of nitrogenated nucleophiles, through an initial attack on gold-activated alkynes followed by gold retrodonation and expulsion of a leaving group, constitutes the most commonly employed strategy for achieving this target. This review has been divided into different sections as follows according to the type of N-nucleophile used: azides, aza-ylides, 2H-azirines, isoxazoles and their derivatives, indazoles, and triazapentalenes. A large number of heterocycles, ranging from five- to seven-membered rings, have been efficiently synthesized following this methodology.

Modern Trends of Organic Chemistry in Russian Universities

Abstract: This review is devoted to the scientific achievements of the departments of organic chemistry in higher schools of Russia within the past decade.