Free download The Chemistry of Heterocyclic Compounds, Supplement I (Chemistry of Heterocyclic Compounds A Series Of Monographs) Volume 58 BY Edward C. Taylor

Volume 58

Authors of:  The Chemistry of Heterocyclic Compounds, Supplement I (Chemistry of Heterocyclic Compounds A Series Of Monographs) Volume 58 BY Edward C. Taylor

Edward c. Taylor  

Peter wipf,

Arnold Weissberger

Table of Contents in The Chemistry of Heterocyclic Compounds, Supplement I (Chemistry of Heterocyclic Compounds A Series Of Monographs) Volume 58 BY Edward C. Taylor

The text provided is a detailed table of contents from a technical book, outlining the synthesis and reactions of pyrazine derivatives, focusing on both aliphatic/carbocyclic synthons and heterocyclic systems. The document is structured into chapters that cover various methods, including syntheses from different atom arrangements, bond completions, and specific chemical reactions of pyrazine derivatives. Here’s a breakdown of the major topics covered:

Chapter 1 focuses on the primary syntheses of pyrazines starting from aliphatic or carbocyclic synthons. This chapter is divided into several sections, starting with single six-atom synthons. It discusses various approaches to synthesize pyrazine derivatives by completing specific bonds within the molecular structure. The first section (1.1) explores syntheses by completing the N-C2 bond, with several subcategories based on different chemical structures, such as azaalkylamines, halogenoazaalkylamines, aminoazaalkanols, and more. For example, the synthesis from appropriate unsaturated azaalkylamines or halogeno(azaalkylamines) is explained with specific focus on how these compounds contribute to the formation of pyrazine derivatives.

Following this, section 1.2 expands on syntheses involving two synthons, specifically looking at combinations of one-atom and five-atom synthons, as well as two-atom and four-atom synthons. Each of these subcategories examines how different atom arrangements, such as one-atom providing nitrogen (N1) or two-atom synthons supplying nitrogen-carbon (N1-C2), affect the overall synthesis process. More complex cases involve two three-atom synthons, where identical or different synthons contribute to the formation of the pyrazine ring. The focus is on completing the N1-C2-C3 bond using various chemical approaches.

Chapter 2 shifts focus to pyrazines derived from other heterocyclic systems. This chapter explores how different heteromonocyclic systems, such as azepines, azetes, azirines, and furans, serve as substrates for pyrazine synthesis. Each section details how these substrates are transformed into pyrazines, using specific reactions and methods. For example, azepines and furans are discussed as substrates for forming pyrazine derivatives, highlighting the different pathways that lead to the desired molecular structures.

In addition, this chapter examines heterobicyclic systems and how they contribute to pyrazine formation. Substrates such as 1,2-diazabicyclohexanes and furo[2,3-b]pyrazines are highlighted, showcasing how these bicyclic compounds are transformed into pyrazines. The chapter concludes by looking at heterotricyclic systems and spiro heterocycles as additional sources for pyrazine derivatives, providing a comprehensive overview of how pyrazines can be synthesized from a wide variety of chemical systems.

Chapter 3 delves into pyrazine itself, along with alkyl- and arylpyrazines. It begins by discussing the preparation and properties of pyrazine, detailing its synthesis and the different reactions it undergoes. Following this, the chapter covers C-alkyl- and C-arylpyrazines, discussing various methods of alkylation and arylation. These include direct C-alkylation, replacement of halogeno substituents, and interconversion of simple alkyl groups. This section also examines how C-alkylation is used in specific synthetic processes, such as the Schöllkopf synthesis, to create more complex pyrazine derivatives. The section on reactions of alkyl- and arylpyrazines addresses oxidative and reductive reactions, extranuclear alkylation, halogenation, and acylation.

Moving on, Chapter 4 discusses halogenopyrazines, focusing on the preparation and reactions of nuclear and extranuclear halogenopyrazines. This chapter breaks down different methods for introducing halogen atoms into the pyrazine ring, such as direct halogenation and deoxidative halogenation. The reactions of these halogenated pyrazines, including aminolysis, hydrolysis, and hydrogenolysis, are covered in detail. Each subsection provides insights into how these reactions alter the properties and behavior of halogenopyrazines.

Chapter 5 focuses on oxypyrazines, starting with tautomeric pyrazinones and their reactions, such as conversion into thiones and N- or O-alkylated derivatives. The chapter continues with extranuclear hydroxypyrazines, alkoxy- or aryloxypyrazines, and non-tautomeric pyrazinones, outlining how these compounds are prepared and how they react under different conditions. Reactions like O-alkylation, acylation, and oxidation are explained in this context, providing a thorough understanding of how these pyrazine derivatives behave chemically.

In Chapter 6, the topic of thiopyrazines is explored. Pyrazinethiones and pyrazinethiols are discussed, along with their methods of preparation and the reactions they undergo, such as oxidation to sulfoxides or sulfones. The chapter also covers alkylthiopyrazines, dipyrazinyl sulfides, and pyrazine sulfoxides and sulfones, explaining their synthesis and chemical behavior in various reactions.

Chapter 7 turns to nitropyrazines, aminopyrazines, and related compounds, starting with methods for preparing nitropyrazines and the reactions they participate in, such as hydrogenation and cyclization. This is followed by discussions on nitrosopyrazines and aminopyrazines, including their preparation and subsequent reactions, such as acylation, alkylation, and ureidation. The chapter also touches on hydrazinopyrazines and azidopyrazines, focusing on how these compounds are synthesized and how they react under specific conditions.

Chapter 8 covers pyrazinecarboxylic acids and related derivatives, outlining methods of preparing pyrazinecarboxylic acids, esters, halides, amides, and other derivatives. Each section provides detailed descriptions of the reactions these compounds undergo, such as esterification, amidation, and the formation of nitriles and ketones.

Overall, the text presents a comprehensive overview of pyrazine chemistry, including the various ways in which pyrazine derivatives can be synthesized and manipulated. Through detailed descriptions of bond completions, atom synthons, and reaction mechanisms, the text offers a deep dive into the world of pyrazine derivatives, providing a valuable resource for chemists working in this field.

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