Tautomeric Schiff bases: Iono-, solvato-, thermo- and photochromism

Publishing nearly 500 original articles a year, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry. The Bulletin's International Advisory Board is comprised of eminent scientists from Europe, USA and Japan. Contributed by leading scientists from Russia and throughout the world, all papers are rigorously refereed and edited to the highest international standards. The Journal was founded in 1936 and has been published in English since 1951. Russian Chemical Bulletin is a translation of the peer-reviewed Russian journal Izvestiya Akademii Nauk: Seriya Khimicheskaya.

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Russian Chemical Bulletin

Synthesis of Diheteroatomic Five‐Membered Heterocyclic Compounds from α,β‐Unsaturated Aldehydes

This review provides comprehensive data (from the author's work and the literature) on tautomerism of pyrazoles, imidazoles, 1,2,3- and 1,2,4-triazoles, tetrazoles, benzimidazoles, benzimidazolones, benzotriazoles, and related compounds by multinuclear 1 H, 13 C, 15 N nuclear magnetic resonance (NMR) spectroscopy. Emphasis is given to studies of azoles by multinuclear dynamic NMR spectroscopy because prototropic transformations of almost all azoles in solution proceed so quickly. Quantum-chemical investigations of tautomeric azoles are covered in detail. Critical analysis of literature data on the tautomerism of azoles is presented. Theoretical studies of structure and reactivity of azoles are most intriguing because correct interpretation of their chemical behavior and biological activity depends on an understanding the factors determining relative stability of their tautomers. 15 N NMR spectroscopy is the most reliable and fast technique for structural and tautomeric determination of nitrogen-containing heteroaromatic compounds.

Tautomerism and Structure of Azoles: Nuclear Magnetic Resonance Spectroscopy

New atranes and similar ionic complexes. Synthesis, structure, properties

Hydrolysis of (Z)-2-alkoxy-3-arylpropenals as a short-cut to benzylglyoxals

Reaction of 2-alkoxy- and 2-hydroxypropenals with o -phenylenediamine: a route to benzimidazoles and quinoxalines

2-(1′-alkoxyvinyl) thiazolidines: synthesis and study of ring-chain tautomerism

The reaction of 2-alkoxypropenals with organylthiols in the presence of small amounts of a base afforded 3-organylsulfanyl-2-alkoxypropanals. The regiochemistry follows the 1,4-addition pattern and contrasts the orientation of the Markovnikov addition, which takes place in the absence of a base. Microwave irradiation accelerates the 1,4-addition reaction.

The Michael addition of organylthiols to 2-alkoxypropenals

A method, allowing alkylthioethanals to be synthesized in 80-93% yields, has been developed. It comprises the hydrolysis of bis-1,1-alkoxy-2-alkylthioethanes using two-phase system water organic solvent. The method is applicable for both common aldehydes bearing lower radicals (R = Pr, Bu) and hitherto unknown highly boiling aldehydes (R = C7H15, C8H17, PhCH2). It has been found that alkylthioethanals can spontaneously trimerize into 2,4,6-alkylthiotrioxanes. In basic media (1N NaOH, KF/Si(OEt)4/EtOH), alkylthioethanals affords the products of aldol selfcondensation in up to 60% yield ( 1 H NMR). In competitive interaction (cross-aldol condensation) of butylthio- and alkoxyethanals with furan- or thiophen-2-carbaldehydes, the reactivity of sulfur-containing carbanions was shown to be more than six times higher than that of the alkoxy analogs.

https://www.arkat-usa.org/get-file/40310/

Yurii A. Chuvashev

Papers

Hydrolysis of (Z)-2-alkoxy-3-arylpropenals as a short-cut to benzylglyoxals

Reaction of 2-alkoxy- and 2-hydroxypropenals with o -phenylenediamine: a route to benzimidazoles and quinoxalines

2-(1′-alkoxyvinyl) thiazolidines: synthesis and study of ring-chain tautomerism

The Michael addition of organylthiols to 2-alkoxypropenals

Synthesis and properties of alkylthioethanals