MCRs reshaped into a switchable microwave-assisted protocol toward 5-aminoimidazoles and dihydrotriazines

Christan E. Bell, Arthur Y. Shaw, Fabio De Moliner, Christopher Hulme

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

A tunable microwave-assisted protocol for the synthesis of two biologically relevant families of heterocycles has been designed. Via a simple switch of reaction conditions, the same starting materials can be engaged in either an improved synthesis of the dihydrotriazine scaffold or a novel, first-in-class MCR to render the challenging 5-aminoimidazole nucleus in a single step. An additional first-in-class MCR is also reported utilizing guanidines to afford 2,5-aminoimidazoles.

Original languageEnglish (US)
Pages (from-to)54-59
Number of pages6
JournalTetrahedron
Volume70
Issue number1
DOIs
StatePublished - Jan 7 2014

Fingerprint

Microwaves
Guanidines
Scaffolds
Switches
4-aminoimidazole
2-aminoimidazole

Keywords

  • Imidazole
  • Multicomponent reaction
  • Strecker
  • Trimethylsilyl cyanide

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

MCRs reshaped into a switchable microwave-assisted protocol toward 5-aminoimidazoles and dihydrotriazines. / Bell, Christan E.; Shaw, Arthur Y.; De Moliner, Fabio; Hulme, Christopher.

In: Tetrahedron, Vol. 70, No. 1, 07.01.2014, p. 54-59.

Research output: Contribution to journalArticle

Bell, Christan E. ; Shaw, Arthur Y. ; De Moliner, Fabio ; Hulme, Christopher. / MCRs reshaped into a switchable microwave-assisted protocol toward 5-aminoimidazoles and dihydrotriazines. In: Tetrahedron. 2014 ; Vol. 70, No. 1. pp. 54-59.
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