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One-pot synthesis of aryl and heteroaroyl-substituted hydroxypyrazolines from the reactions of β-alkoxyvinyl trichloromethyl ketones with heteroarylhydrazides

✍ Scribed by Helio G. Bonacorso; Marli R. Oliveira; Michelle B. Costa; Roberta L. Drekener; Letícia B. da Silva; Nilo Zanatta; Marcos A. P. Martins

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
130 KB
Volume
17
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

The one‐step regiospecific synthesis of a novel series of 10 trichloromethyl‐, aryl‐, and heteroaroyl‐substituted 5‐hydroxy‐2‐pyrazolines affords 1‐(2‐thenoyl)‐, 1‐(2‐furoyl)‐, and 1‐(isonicotinoyl)‐3‐aryl‐5‐hydroxy‐5‐trichloromethyl‐4,5‐dihydro‐1H‐pyrazoles in 63–92% yields from the cyclocondensation reactions of 1,1,1‐trichloro‐4‐methoxy‐4‐aryl‐3‐buten‐2‐ones (where aryl substituents are –C~6~H~5~, 4‐CH~3~C~6~H~4~, 4‐OCH~3~C~6~H~4~, 4‐FC~6~H~4~, 4‐ClC~6~H~4~, 4‐BrC~6~H~4~) with 2‐thiophenecarboxylic hydrazide, furoic hydrazide, and isonicotinic acid hydrazide, respectively. Dehydration reaction of two 2‐pyrazolines with P~2~O~5~ furnished the corresponding 1H‐pyrazoles in low yields (21–29%). © 2006 Wiley Periodicals, Inc. Heteroatom Chem 17:685–691, 2006; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20261

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