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The synthesis of 3,3-dimethyl-2-(1-aryl-1h-pyrazol-4-yl)-3h-indoles

✍ Scribed by Mehdi M. Baradarani; Arash Afghan; Farideh Zebarjadi; Kamal Hasanzadeh; John A. Joule

Publisher: Journal of Heterocyclic Chemistry
Year: 2006
Tongue: English
Weight: 273 KB
Volume: 43
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570430624

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✦ Synopsis

Abstract

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2,3,3‐Trimethylindolenine and 5‐chloro‐2,3,3‐trimethylindolenine were converted into β‐diformyl compounds by the action of the Vilsmeier reagent at 50°C. The dialdehydes reacted with various arylhydrazines and 2‐pyridylhydrazine to produce mono‐hydrazones as mixtures of cis and trans isomers. Heating the hydrazones in refluxing ethanol produced 3,3‐dimethyl‐2‐(1‐aryl‐1__H__‐pyrazol‐4‐yl)‐3__H__‐indoles in excellent yields. Reaction of the β‐diformyl compounds with hydrazine itself led directly to 3,3‐dimethyl‐2‐(pyrazol‐4‐yl)‐3__H__‐indoles.

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