Synthesis of some thiochromeno[4,3-c]- and [3,4-c]-pyrazoles

Christopher D. Gabbutt, John D. Hepworth, B. Mark Heron, Simon J. Coles, Michael B. Hursthouse

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Reaction of 3-hydroxymethylene- and 3-cyanomethylene-thiochroman-4-ones with various hydrazine derivatives affords 4H-thiochromeno[4,3-c]pyrazoles. The novel isomeric thiochromeno[3,4-c]pyrazoles result when 4-(dimethylaminomethylene)thiochroman-3-ones react with methyl- and phenyl-hydrazines. Acidic hydrolysis of 3-(dimethylhydrazonoethylidene)-2,2,6-trimethylthiochroman-4-one yields the 3-cyanomethylene-thiochroman-4-one. Formation of 6-chloro-3-hydroxymethylenethiochroman-4-one is accompanied by a thiochroman-3-yl(oxothiochromen-3-yl)methane derivative produced through a rearrangement-carbocation interception sequence. A 3-isopropenylthiochromenone, obtained by the acid promoted rearrangement of a 3-hydroxymethylenethiochroman-4-one, undergoes Diels-Alder cycloadditions to provide a new route to thioxanthenones.

LanguageEnglish
Pages2930-2938
Number of pages9
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number17
DOIs
Publication statusPublished - 1 Jan 2000
Externally publishedYes

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Pyrazoles
hydrazine
Hydrazines
Derivatives
Cycloaddition
Methane
Hydrolysis
Acids

Cite this

Gabbutt, Christopher D. ; Hepworth, John D. ; Heron, B. Mark ; Coles, Simon J. ; Hursthouse, Michael B. / Synthesis of some thiochromeno[4,3-c]- and [3,4-c]-pyrazoles. In: Journal of the Chemical Society, Perkin Transactions 1. 2000 ; No. 17. pp. 2930-2938.
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Synthesis of some thiochromeno[4,3-c]- and [3,4-c]-pyrazoles. / Gabbutt, Christopher D.; Hepworth, John D.; Heron, B. Mark; Coles, Simon J.; Hursthouse, Michael B.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 17, 01.01.2000, p. 2930-2938.

Research output: Contribution to journalArticle

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