Thermal reaction of sodium salts of α-nitrohydrazones with arylidenemalonitriles and α,β-unsaturated ketones
A mixture of sodium salt of (α-nitroethylidene)-p-tolylhydrazine (1b) and arylidenemalonitriles (3a-g) when refluxed in acetonitriles gives 5-cyano-1,3-diaryl-3-methylpyrazoles (6a-g) reespectively.Similar reaction of 1 and benzyldieneacetophenones (4) yields 5-aroyl-1,4-diaryl-3-methyl-2-pyrazolines (7).Formation of 6 and 7 can be visualised as involving intermolecular cycloaddition of nitrilimines (2) generated in situ via thermal elimination of sodium nitrite from 1 to the dipolarophiles 3 and 4 respectively.
Hassaneen, Hamdi M.,Shawali, Ahmad S.
p. 133 - 135
(2007/10/02)
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