Five-membered heterocyclic compounds with two nitrogen atoms in the ring

R.S. Theobald

Research output: Chapter in Book/Report/Conference proceedingChapter

Abstract

Five-membered aromatic systems with two ring nitrogen atoms are known as diazoles, and the isomer in which these nitrogens are adjacent is pyrazole. Thus, pyrazole can be regarded as a composite of the pyrrole and pyridine structures. In this chapter, methods of preparation, general properties of the ring system, and typical chemical reactions of the pyrazoles are discussed. The various homologs and derivatives of pyrazole are analyzed, such as the pyrazole-2-oxides, N-alkyl and N-aryl derivatives, N-acylpyrazoles, C-alkyl and C-Aryl derivatives, halogenopyrazoles, nitroso- and nitro-pyrazoles, amino and diazo compounds, cyanopyrazoles, aldehydes and ketones, carboxylic acids and derivatives and reduced systems. Indazole, or benzopyrazole, bears the same relation to pyrazole as indole does to pyrrole. Isomeric with pyrazole, the imidazole system carries its two nitrogen atoms in the alternative relationship, with an intervening methine group. The imidazole ring system occurs widely in nature, from the simple amino-acid histidine, to the imidazole alkaloids, such as pilocarpine, the purines and the imidazole nucleosides. The discovery of the 5,6-dimethylbenzimidazole unit in the vitamin B12 structure stimulated interest in the synthetic methods of benzimidazoles; they include systemic fungicides, such as benomyl, several veterinary anthelmintics, and PBI, a highly thermostable polybenzimidazole with specialist textile uses.
LanguageEnglish
Title of host publicationRodd's Chemistry of Carbon Compounds
Subtitle of host publicationA Modern Comprehensive Treatise
PublisherElsevier
Pages1-242
Number of pages242
Volume4
Edition2nd
ISBN (Print)9780444533456
DOIs
StatusPublished - 1964

Fingerprint

Heterocyclic Compounds
Nitrogen
Atoms
Pyrazoles
Derivatives
Pyrroles
Indazoles
Benomyl
Benzimidazoles
Fungicides
Purines
Pilocarpine
Anthelmintics
Vitamin B 12
Carboxylic Acids
Ketones
Nucleosides
Alkaloids
Histidine
Aldehydes

Cite this

Theobald, R. S. (1964). Five-membered heterocyclic compounds with two nitrogen atoms in the ring. In Rodd's Chemistry of Carbon Compounds: A Modern Comprehensive Treatise (2nd ed., Vol. 4, pp. 1-242). Elsevier. DOI: 10.1016/B978-044453345-6.50717-3

Five-membered heterocyclic compounds with two nitrogen atoms in the ring. / Theobald, R.S.

Rodd's Chemistry of Carbon Compounds: A Modern Comprehensive Treatise. Vol. 4 2nd. ed. Elsevier, 1964. p. 1-242.

Research output: Chapter in Book/Report/Conference proceedingChapter

Theobald, RS 1964, Five-membered heterocyclic compounds with two nitrogen atoms in the ring. in Rodd's Chemistry of Carbon Compounds: A Modern Comprehensive Treatise. 2nd edn, vol. 4, Elsevier, pp. 1-242. DOI: 10.1016/B978-044453345-6.50717-3
Theobald RS. Five-membered heterocyclic compounds with two nitrogen atoms in the ring. In Rodd's Chemistry of Carbon Compounds: A Modern Comprehensive Treatise. 2nd ed. Vol. 4. Elsevier. 1964. p. 1-242. Available from, DOI: 10.1016/B978-044453345-6.50717-3
Theobald, R.S./ Five-membered heterocyclic compounds with two nitrogen atoms in the ring. Rodd's Chemistry of Carbon Compounds: A Modern Comprehensive Treatise. Vol. 4 2nd. ed. Elsevier, 1964. pp. 1-242
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