Thiopyrans and their benzo derivatives

J. D. Hepworth, B. M. Heron

Research output: Chapter in Book/Report/Conference proceedingChapter

12 Citations (Scopus)

Abstract

The chemistry of thiopyrans, thiopyranones, and thiopyrylium salts and of their benzologues and reduced derivatives are covered. Structural details derived from X-ray and microwave studies are supported by information obtained using NMR, UV, IR, and ESR spectroscopy and mass spectrometry. Aromatic character of the heterocycles is discussed and attention paid to their conformations and tautomeric behavior. Examples of the application of molecular modeling to these molecules are provided.

Reactivity of electrophiles, nucleophiles and species possessing unpaired electrons at C, S, and H are reviewed and oxidation of the S heteroatom is described. The behavior of the heterocycles as dienes and dienophiles in cycloaddition reactions is considered. Reactions of substituents at both C and S are described.

The synthesis of these six-membered S-heterocycles is separated into methods of value for the formation of thiopyrans, thiopyranones, and thiopyrylium salts and further subdivided according to the location of the heteroatom with respect to the functionality.

These heterocyclic systems are of value in a variety of situations and their applications in biological and pharmaceutical areas are reviewed, paying particular attention to the patent literature. Finally, the potential of these molecules in materials chemistry is discussed.
Original languageEnglish
Title of host publicationComprehensive Heterocyclic Chemistry III
EditorsAlan R. Katritzky, Christopher A. Ramsden, Richard J.K. Taylor
PublisherElsevier Ltd
Pages727-954
Number of pages228
Volume7
ISBN (Print)9780080449920
DOIs
Publication statusPublished - 2008
Externally publishedYes

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Hepworth, J. D., & Heron, B. M. (2008). Thiopyrans and their benzo derivatives. In A. R. Katritzky, C. A. Ramsden, & R. J. K. Taylor (Eds.), Comprehensive Heterocyclic Chemistry III (Vol. 7, pp. 727-954). Elsevier Ltd. https://doi.org/10.1016/B978-008044992-0.00610-6