Quinoxalines

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.

The first and only book that comprehensively describes the opportunities quinoxalines offer as reagents for the synthesis of biologically important condensed derivatives The book explains new acid-catalyzed rearrangements of quinoxalinones giving benzimidazoles when exposed to nucleophilic reactants, thus leading to biheterocyclic systems The understanding of the methods and mechanisms of the reactions presented will allow synthetic chemists to extend these ideas to other processes in achieving their goals Includes supplementary material: sn.pub/extras

Autorentext
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.

Inhalt

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.