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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 19
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Articles

A convenient synthesis of functionalized pyrazolones bearing a highly twisted 1,3-butadiene moiety with skew geometry

Issa YavariDepartment of Chemistry, Tarbiat Modares University, Tehran, Iran; Correspondence[email protected]
,
Jamil SheykhahmadiDepartment of Chemistry, Tarbiat Modares University, Tehran, Iran;
,
Hamed SaffarianDepartment of Chemistry, Tarbiat Modares University, Tehran, Iran;
,
Nooshin ZahediDepartment of Chemistry, Tarbiat Modares University, Tehran, Iran;
,
Samira BahemmatDepartment of Inorganic Chemistry, Chemistry and Chemical Engineering Research Centre of Iran, Tehran, Iran
&
Mohammad Reza HalvagarDepartment of Inorganic Chemistry, Chemistry and Chemical Engineering Research Centre of Iran, Tehran, Iran
Pages 2608-2614 | Received 04 Apr 2018, Published online: 10 Oct 2018
 
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Abstract

The four-component reaction among arylhydrazine, alkyl acetoacetate derivatives, alkyl isocyanides, and dialkyl acetylenedicarboxylates, leading to the formation of dialkyl 2-[(Z)-(alkylamino)(3-alkyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)methyl] fumarates is described. The structure of target compounds was confirmed using X-ray diffraction study. These pyrazolone derivatives contain a highly twisted exocyclic 1,3-butadiene moiety with skew (ϕ = 87°) geometry.

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