Facile synthesis of 1H-imidazo[1,2-b]pyrazoles via a sequential one-pot synthetic approach

András Demjén, Márió Gyuris, J. Wölfling, L. Puskás, Iván Kanizsai

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

5-Aminopyrazole-4-carbonitrile and ethyl 5-aminopyrazole-4-carboxylate, as potential trifunctional building blocks are introduced in a facile, chemo- and regioselective multicomponent assembly of imidazo[1,2-b]pyrazoles via the Groebke-Blackburn-Bienaymé reaction (GBB reaction). Besides the synthetic elaboration of a green-compatible isocyanide-based access in three-component mode, we describe an operationally simple, one-pot two-step GBB protocol for the rapid construction of a 46 membered imidazo[1,2- b ] pyrazole library with yields up to 83%.

Original languageEnglish
Pages (from-to)2338-2344
Number of pages7
JournalBeilstein Journal of Organic Chemistry
Volume10
DOIs
Publication statusPublished - Oct 8 2014

Fingerprint

imidazopyrazole
Pyrazoles
Cyanides
5-aminopyrazole

Keywords

  • 1H-imidazo[1,2-b]pyrazole
  • Groebke-Blackburn-Bienaymé reaction
  • Isocyanide
  • Multicomponent reaction
  • N-heterocycles

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Facile synthesis of 1H-imidazo[1,2-b]pyrazoles via a sequential one-pot synthetic approach. / Demjén, András; Gyuris, Márió; Wölfling, J.; Puskás, L.; Kanizsai, Iván.

In: Beilstein Journal of Organic Chemistry, Vol. 10, 08.10.2014, p. 2338-2344.

Research output: Contribution to journalArticle

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AU - Puskás, L.

AU - Kanizsai, Iván

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