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

✍ Scribed by Claudete J. Valduga; Hugo S. Braibante; Mara E. F. Braibante

Publisher
Journal of Heterocyclic Chemistry
Year
1997
Tongue
English
Weight
323 KB
Volume
34
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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 was systematically studied when allowed to react with hydrazine and methylhydrazine under solid support K‐10/ultrasound conditions and in homogeneous media (reflux in ethanol or dichloromethane). The products were pyrazoles 2a‐d, N‐methylpyrazoles 3a‐d, 4a‐d and N‐methylpyrazolinones 6a‐c and 7a‐c. The regiochemistry of the cyclization reactions showed dependence upon the reaction conditions employed as well as upon the sub‐stituent in the aromatic ring.

📜 SIMILAR VOLUMES

ChemInform Abstract: Reactivity of p-Phe
ChemInform Abstract: Reactivity of p-Phenyl Substituted β-Enamino Compounds Using K-10/Ultrasound. Part 1. Synthesis of Pyrazoles and Pyrazolinones.
✍ C. J. VALDUGA; H. S. BRAIBANTE; M. E. F. BRAIBANTE 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 37 KB 👁 1 views

Reactivity of p-Phenyl Substituted β-Enamino Compounds Using K-10/Ultrasound. Part 1. Synthesis of Pyrazoles and Pyrazolinones. -In order to examine the reactivity of the electrophilic center in the β-enamino ketones (I) and esters (VI) these compounds are reacted with hydrazine and methylhydrazine

ChemInform Abstract: Reactivity of p-Phe
ChemInform Abstract: Reactivity of p-Phenyl Substituted β-Enamino Compounds Using K-10/Ultrasound. Part 1. Synthesis of Pyrazoles and Pyrazolinones.
✍ C. J. VALDUGA; H. S. BRAIBANTE; M. E. F. BRAIBANTE 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 34 KB 👁 1 views

Reactivity of p-Phenyl Substituted β-Enamino Compounds Using K-10/Ultrasound. Part 1. Synthesis of Pyrazoles and Pyrazolinones. -In the reaction with unsubstituted hydrazine it is not clarified which of the both forms (II) or (III) is obtained. -(VALDUGA, C.

Reactivity of p-phenyl substituted β-Ena
Reactivity of p-phenyl substituted β-Enamino compounds using K-10/ultrasound. II. Synthesis of isoxazoles and 5-Isoxazolones
✍ Claudete J. Valduga; Denise B. Santis; Hugo S. Braibante; Mara E. F. Braibante 📂 Article 📅 1999 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 215 KB

## Abstract The condensation of 4‐phenyl substituted β‐enamino ketones 1a‐d and β‐enamino esters 5a‐d with hydroxylamine hydrochloride using K‐10 as the solid support under sonication was studied to evaluate the formation of isoxazole and 5‐isoxazolone rings from β‐enamino compounds with a substitu