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

Alizadeh Abdolali | Zendy; Reza Esmaili zand Hamid | Zendy; Saberi Vahid | Zendy; Mokhtari Javad | Zendy

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

Author(s) -

Alizadeh Abdolali,

Reza Esmaili zand Hamid,

Saberi Vahid,

Mokhtari Javad

Publication year - 2013

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.201300070

Subject(s) - chemistry , hydrazine (antidepressant) , component (thermodynamics) , aryl , medicinal chemistry , proton nmr , reaction mechanism , organic chemistry , catalysis , chromatography , alkyl , physics , thermodynamics

An efficient approach for the preparation of functionalized 5‐aryl‐3‐(methylsulfanyl)‐1 H ‐pyrazoles 2 is described. This three‐component reaction between benzaldehydes 1 , NH 2 NH 2 ⋅H 2 O, 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, 1 H‐ and 13 C‐NMR, and EI‐MS). A plausible mechanism for this type of reaction is proposed ( Scheme 2 ).

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