'One-pot' synthesis of 4-substituted 1,5-diaryl-1H-pyrazole-3-carboxylates via lithium tert-butoxide-mediated sterically hindered Claisen condensation and Knorr reaction

Jian An Jiang, Wei Bin Huang, Jiao Jiao Zhai, Hong Wei Liu, Qi Cai, Liu Xin Xu, Wei Wang, Ya Fei Ji

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

A concise 'one-pot' synthesis of a variety of 4-substituted 1,5-diaryl-1H-pyrazole-3-carboxylates has been developed in moderate to good yields with excellent regioselectivity. Less cost lithium tert-butoxide has been identified as a base for sterically hindered Claisen condensation to efficiently generate the labile 3-substituted 4-aryl-2,4-diketoesters. Furthermore, extensive studies lead to a 'one-pot' process by combination of the Claisen condensation and the Knorr reaction for the synthesis of highly valuable 4-substituted 1,5-diaryl-1H-pyrazole-3-carboxylates.

Original languageEnglish (US)
Pages (from-to)627-635
Number of pages9
JournalTetrahedron
Volume69
Issue number2
DOIs
StatePublished - Jan 14 2013
Externally publishedYes

Keywords

  • 3-substituted 4-aryl-2,4-diketoesters
  • 4-substituted 1,5-diaryl-1H-pyrazole-3-carboxylates
  • Knorr reaction
  • Lithium tert-butoxide
  • Sterically hindered Claisen condensation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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