A one-pot approach to ethyl 1,4,5-triaryl-1H-pyrazole-3-carboxylates via an improved claisen condensation-knorr reaction sequence

Jiaojiao Zhai, Chunhui Gu, Jianan Jiang, Shunli Zhang, Daohua Liao, Lei Wang, Dunru Zhu, Yafei Ji

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8 Scopus citations

Abstract

A one-pot approach to ethyl 1,4,5-triaryl-1H-pyrazole-3-carboxylates has been developed in moderate to high yields. The tert-BuOLi-mediated Claisen condensation of 1,2-diarylethanones and ethyl oxalyl chloride efficiently provided the enolized lithium salts of ethyl 2,4-dioxo-3,4-diarylbutanoates, which in situ reacted with arylhydrazine hydrochlorides via a hydrochloric acid-promoted Knorr reaction to produce the exquisite triarylpyrazole-3- carboxylates. The procedure promises a convenient access to this highly crowded framework for drug discovery.

Original languageEnglish
Pages (from-to)1526-1538
Number of pages13
JournalChinese Journal of Chemistry
Volume31
Issue number12
DOIs
StatePublished - Dec 2013

Keywords

  • 2,4-dioxo-3,4-diarylbutanoates
  • Claisen condensation
  • Knorr reaction
  • one-pot approach
  • triarylpyrazole-3-carboxylates

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