Five-Membered Heterocyclic Compounds with Four Hetero-Atoms in the Ring

Research output: Chapter in Book/Report/Conference proceedingChapter

Abstract

This chapter discusses the five-membered heterocyclic compounds with four hetero-atoms in the ring. The compounds of tetrazolesmay be referred to one or other of the tautomeric 1H- or 2H- structures. Tetrazoles require the addition of azides to nitriles. 5-Alkoxy- and 5-aryloxy-tetrazoles are found from the interaction of cyanic esters and azide ion. Tetrazole-5-aldehyde is prepared by the action of hydrazoic acid upon diethoxyacetonitrile. Sulfur containing mesoionic tetrazoles are also known, of which the most commonly encountered is 2,3-diphenyl 2-H-tetrazolium-5-thiolate, often called dehydrodithizone. Nitrosation of the arylhydrazinium dithiocarbamates affords 1,2,3,4-oxatriazolium-5-thiolates, which in the presence of ammonia and ethanol rearrange to 1,2,3,4-thiatriazolium-5-olates. 1,2,3,5-Oxatriazolium salts are synthesized by the diazotization of 2-aminopyridine-l-oxide. 1,2,3,4-Thiatriazoles are compounds with a long and sometimes controversial existence. The usual synthesis of 5-substituted 1,2,3,4-thiatriazoles involves the reaction of thioacylhydrazines with nitrous acid. Thioacylazides are converted directly into 5-alkyl derivatives. In turn the azides are formed as intermediates in the reaction of 1-acetylthio-1-alkynes and ammonium azide. Such compounds are rare, but representative structures can be prepared by addition reactions of nitrile oxides and suitable reagents. 3H-1,2,3,5-oxathiadiazoles are formed and 1,3,2,4-dioxathiazole-2,2-dioxides are produced when sulfur trioxide is used.
LanguageEnglish
Title of host publicationRodd's Chemistry of Carbon Compounds
Subtitle of host publicationA Modern Comprehensive Treatise
PublisherElsevier
Pages211-246
Number of pages36
Volume4
Edition2nd
ISBN (Print)9780444533456
DOIs
StatusPublished - 1964

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Heterocyclic Compounds
Tetrazoles
Azides
Atoms
Nitriles
Oxides
Nitrous Acid
Addition reactions
Alkynes
Ammonium Compounds
Ammonia
Sulfur
Aldehydes
Esters
Ethanol
Salts
Ions
Derivatives

Cite this

Sainsbury, M. (1964). Five-Membered Heterocyclic Compounds with Four Hetero-Atoms in the Ring. In Rodd's Chemistry of Carbon Compounds: A Modern Comprehensive Treatise (2nd ed., Vol. 4, pp. 211-246). Elsevier. DOI: 10.1016/B978-044453345-6.50728-8

Five-Membered Heterocyclic Compounds with Four Hetero-Atoms in the Ring. / Sainsbury, M.

Rodd's Chemistry of Carbon Compounds: A Modern Comprehensive Treatise. Vol. 4 2nd. ed. Elsevier, 1964. p. 211-246.

Research output: Chapter in Book/Report/Conference proceedingChapter

Sainsbury, M 1964, Five-Membered Heterocyclic Compounds with Four Hetero-Atoms in the Ring. in Rodd's Chemistry of Carbon Compounds: A Modern Comprehensive Treatise. 2nd edn, vol. 4, Elsevier, pp. 211-246. DOI: 10.1016/B978-044453345-6.50728-8
Sainsbury M. Five-Membered Heterocyclic Compounds with Four Hetero-Atoms in the Ring. In Rodd's Chemistry of Carbon Compounds: A Modern Comprehensive Treatise. 2nd ed. Vol. 4. Elsevier. 1964. p. 211-246. Available from, DOI: 10.1016/B978-044453345-6.50728-8
Sainsbury, M./ Five-Membered Heterocyclic Compounds with Four Hetero-Atoms in the Ring. Rodd's Chemistry of Carbon Compounds: A Modern Comprehensive Treatise. Vol. 4 2nd. ed. Elsevier, 1964. pp. 211-246
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