Quinoxalines: Synthesis, Reactions, Mechanisms and Structure

ISBN-13: 9783319297712 / Angielski / Twarda / 2016 / 437 str.

Vakhid Mamedov

Opis

This book reviews the fundamental aspects of quinoxaline chemistry: synthesis, reactions, mechanisms, structure, properties, and applications. The first five chapters present a survey of the developments in quinoxaline chemistry since the publication of the monograph Condensed Pyrazines by Cheeseman and Cookson in 1979. These chapters give a comprehensive coverage of the important quinoxaline-containing ring systems such as thiazolo 3,4-"a"]-, pyrrolo 1,2-"a"]-, imidazo 1,5-"a"]quinoxalines, etc. The remaining sixth chapter gives a review of all the previously known rearrangements of heterocyclic systems that lead to benzimidazole derivatives. A critical analysis of these transformations reveals novel acid-catalyzed rearrangements of quinoxalinones giving 2-heteroarylbenzimidazoles and 1-heteroarylbenzimidazolones in the presence of nucleophilic reactants. Existing literature is thoroughly and critically reviewed.

Spis treści

Introduction: Quinoxaline as a Parent Heterocycle.- Synthesis of Quinoxalines.- Synthesis of Pyrrolo[l,2-a]quinoxalines.- Synthesis of Imidazo[1,5-a]- and Imidazo[1,2-a]quinoxalines.- Synthesis of Quinoxaline Macrocycles.- Rearrangements of Quinoxalin(on)es in the Synthesis of Benzimidazol(on)es.- Appendix.

O autorze

Vakhid A. Mamedov is the Head of Laboratory for the Chemistry of Heterocycles at the Kazan Scientific Centre of the Russian Academy of Sciences. His research is dedicated to quinoaxilines. After his graduation from the Azerbaijan State University in Baku (1981) and working at the Institutes of Physics and of Petroleum and Chemical Processes (1981-1982) of the Azerbaijan Academy of Sciences, he moved to Kazan in 1985, where he received his Ph.D (1989), and D.Sc. (1999) degrees in chemistry, working with the Professors Il’dus A. Nuretdinov, Eugeniy A. Berdnikov and Yakov A. Levin. He spent a postdoctoral fellowship (1997-1998) with Professor Sadao Tsuboi at the Okayama University (Japan), working on synthetic approaches to the C-13 side chain of paclitaxel (Taxol) and docetaxel (Taxotere). He became head of laboratory of the Chemistry of Heterocyclic Compounds in IOPC in 2002. He was principal tutor of 10 post-graduated and 24 graduated students, both in Russia and Japan. He authored over 170 papers. Mamedov’s research interests focus on the methodology of organic synthesis, development of new schemes of the tandem transformations for synthesizing the diversity-oriented heterocyclic systems. 

Blurb

This book reviews the fundamental aspects of quinoxaline chemistry: synthesis, reactions, mechanisms, structure, properties, and uses. The first four chapters present a survey of the developments in quinoxaline chemistry since the publication of the monograph on “Condensed Pyrazines” by Cheeseman and Cookson in 1979. These chapters give comprehensive coverage of all the methods of the synthesis of quinoxalines and  the important quinoxaline-containing ring systems such as thiazolo[3,4-a]-, pyrrolo[1,2-a]-, and imidazo[1,5-a]quinoxalines. Chapter five describes many new methods for the construction of quinoxaline macrocycles, which are important in applications such as optical devices and materials. The final chapter reviews all previously known rearrangements of heterocyclic systems that lead to benzimidazole derivatives. Mamedov critically analyses these transformations to reveal a novel acid-catalyzed rearrangement of quinoxalinones giving 2-heteroarylbenzimidazoles and 1-heteroarylbenzimidazolones in the presence of nucleophilic reactants (MAMEDOV Heterocycle Rearrangement). This book is of interest to researchers in the fields of heterocyclic and synthetic organic chemistry.