Reactivity of p-phenyl substituted β-enamino compounds using k-10/ultrasound. I. synthesis of pyrazoles and pyrazolinones

The reactivity of the β‐enamino ketones, 3‐amino‐1‐(p‐phenyl‐substituted)‐2‐buten‐1‐ones 1a‐d and β‐enamino esters. Ethyl‐3‐amino‐3‐(p‐phenyl‐substituted)‐2‐propenoates 5a‐d were evaluated by systematic studies of the reactions with hydrazine and methylhydrazine by reactions with solid support K‐10/...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 1998-01, Vol.35 (1), p.189-192
Main Authors: Valduga, Claudete J., Braibante, Hugo S., Braibante, Mara E. F.
Format: Article
Language:English
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Summary:The reactivity of the β‐enamino ketones, 3‐amino‐1‐(p‐phenyl‐substituted)‐2‐buten‐1‐ones 1a‐d and β‐enamino esters. Ethyl‐3‐amino‐3‐(p‐phenyl‐substituted)‐2‐propenoates 5a‐d were evaluated by systematic studies of the reactions with hydrazine and methylhydrazine by reactions with solid support K‐10/ultrasound and homogeneous media (reflux in ethanol or dichloromethane) yielding pyrazole rings 2a‐d, N‐methylpyrazoles 3a‐d, 4a‐d and N‐methylpyrazolinones 6a‐c and 7a‐c. The regiochemistry of the cyclization showed dependence of the reaction conditions employed as well as the substituent in the aromatic ring.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.5570350136