Synthesis of 5-Aryl-3-(methylsulfanyl)-1H-pyrazoles via Three-Component Reaction of 1,1-Bis(methylsulfanyl)-2-nitroethene, Aromatic Aldehydes, and Hydrazine

An efficient approach for the preparation of functionalized 5‐aryl‐3‐(methylsulfanyl)‐1H‐pyrazoles 2 is described. This three‐component reaction between benzaldehydes 1, NH2NH2⋅H2O, and 1,1‐bis(methylsulfanyl)‐2‐nitroethene proceeds in EtOH under reflux conditions in good‐to‐excellent yields. The st...

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Bibliographic Details
Published in:Helvetica chimica acta 2013-12, Vol.96 (12), p.2240-2244
Main Authors: Alizadeh, Abdolali, Reza Esmaili zand, Hamid, Saberi, Vahid, Mokhtari, Javad
Format: Article
Language:English
Subjects:
1-bis(methylsulfanyl)-2-nitro
1H-Pyrazoles
Ethene
Ethene, 1,1‐bis(methylsulfanyl)‐2‐nitro
Hydrazones
Michael addition
Multicomponent reactions
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Summary:An efficient approach for the preparation of functionalized 5‐aryl‐3‐(methylsulfanyl)‐1H‐pyrazoles 2 is described. This three‐component reaction between benzaldehydes 1, NH2NH2⋅H2O, and 1,1‐bis(methylsulfanyl)‐2‐nitroethene proceeds in EtOH under reflux conditions in good‐to‐excellent yields. The structures of 2 were corroborated spectroscopically (IR, 1H‐ and 13C‐NMR, and EI‐MS). A plausible mechanism for this type of reaction is proposed (Scheme 2).
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.201300070