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

Gabbutt, C. D., Hepworth, J. D., Heron, B. M., Coles, S. J. and Hursthouse, M. B. (2000) Synthesis of some thiochromeno 4,3-c - and 3,4-c -pyrazoles Journal of the Chemical Society, Perkin Transactions 1, (17), pp. 2930-2938. (doi:10.1039/b004149l).

Record type: Article


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-cyanomethylenethiochroman-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.

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Published date: 2000
Keywords: cyclic beta-enaminones, substituted pyrazoles, fused heterocycles, stereochemistry, ketones, reactivity


Local EPrints ID: 18868
ISSN: 0300-922X
PURE UUID: b8ad6a49-0385-43de-b326-50d1b971eac3

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Date deposited: 21 Dec 2005
Last modified: 17 Jul 2017 16:34

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Author: C. D. Gabbutt
Author: J. D. Hepworth
Author: B. M. Heron
Author: S. J. Coles
Author: M. B. Hursthouse

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