Synthesis of previously unknown 3,3′-linearly linked sulfur- and selenium-containing bispyrazoles by reactions of 3-alkenyl-5-chloropyrazoles with bischalcogenols

Rudyakova, E. V.; Samultsev, D. O.; Леванова, Е. П.; Levkovskaya, G. G.

doi:10.1134/s1070428013050175

Cited by 7 publications

(1 citation statement)

References 19 publications

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“…[33][34][35] Imidoalkylation of 1-, 3-, 4-, and 5-vinylpyrazoles with N-(2,2,2-trichloroethylidene)ethoxycarbonylamines is also reported 34,36 Chemical transformations of the difficult-to-access 3-alkenylpyrazoles 36-38 and 3-alkenyl-5-chloropyrazoles 28 are even less studied and only very few reactions with oxygen and sulphur nucleophiles have been published. 39,40 We have recently developed methodology for the preparation of hitherto unknown 3-alkenylpyrazoles, 28 possible building blocks for the directed synthesis of substances and materials for advanced technologies, from the corresponding 3-haloalkyl pyrazoles. The aim of the present work is to study of chemical behavior of 3-alkenylpyrazoles in the reactions with aromatic and aliphatic thiols.…”

Section: Introductionmentioning

confidence: 99%

Novel directed synthesis of functionalized pyrazole derivatives via regioselective solvent-free thiylation of 3-alkenylpyrazoles with arenethiols

Levkovskaya¹,

Rudyakova²,

Kobelevskaya³

et al. 2016

Arkivoc

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Unprecedented easy (3 min., room temperature) regioselective addition of thiols to the endocyclic double bond of 3-vinyl-, prop-1-enyl-and isopropenyl, including those with bulky substituents in the position 1 of the pyrazole ring, has been found for the reaction of arenethioles with 3-alkenyl-5-chloropyrazoles. The reaction proceeds under solvent-free and catalyst-free conditions to afford 3-[(2-arylsulfanyl)alkyl]-5-chloropyrazoles in excellent yields. High rate of the process is likely due to protonation of the "pyridine" nitrogen atom of the pyrazole ring to give a pyrazolium ion which activates the vinyl group towards nucleophilic attack by the simultaneously formed arylthiolate anions.

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