Synthesis of diverse nitrogen-enriched heterocyclic scaffolds using a suite of tunable one-pot multicomponent reactions

Guillermo Martinez-Ariza, Muhammad Ayaz, Federico Medda, Christopher Hulme

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Five elegant and switchable three-component reactions which enable access to a new series of nitrogen-containing heterocycles are reported. A novel one-step addition of an isocyanide to a hydrazine derived Schiff base affords unique six-membered pyridotriazine scaffolds (A and E). With slight modification of reaction conditions and replacement of the nucleophilic isocyanide moiety with different electrophiles (i.e., isocyanates, isothiocyanates, cyclic anhydrides, and acyl chlorides) five-membered triazolopyridine scaffolds (B, D, F, G) are generated in a single step. Furthermore, the use of phenyl hydrazine enables access to dihydroindazole-carboxamides, devoid of a bridge-head nitrogen (C). All protocols are robust and tolerate a diverse collection of reactants, and as such, it is expected that the new scaffolds and associated chemistry will garner high interest from medicinal chemists involved in either file enhancement or specific target-related drug discovery campaigns.

Original languageEnglish (US)
Pages (from-to)5153-5162
Number of pages10
JournalJournal of Organic Chemistry
Volume79
Issue number11
DOIs
StatePublished - Jun 6 2014

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hydrazine
Cyanides
Scaffolds
Nitrogen
Isothiocyanates
Isocyanates
Schiff Bases
Anhydrides
Drug Discovery
Chlorides
Head

ASJC Scopus subject areas

  • Organic Chemistry
  • Medicine(all)

Cite this

Synthesis of diverse nitrogen-enriched heterocyclic scaffolds using a suite of tunable one-pot multicomponent reactions. / Martinez-Ariza, Guillermo; Ayaz, Muhammad; Medda, Federico; Hulme, Christopher.

In: Journal of Organic Chemistry, Vol. 79, No. 11, 06.06.2014, p. 5153-5162.

Research output: Contribution to journalArticle

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