Literature DB >> 24535889

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

Christan E Bell1, Arthur Y Shaw2, Fabio De Moliner2, Christopher Hulme2.   

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.

Entities:  

Keywords:  Imidazole; Multicomponent Reaction; Strecker; Trimethylsilylcyanide

Year:  2014        PMID: 24535889      PMCID: PMC3925149          DOI: 10.1016/j.tet.2013.11.035

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  29 in total

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5.  Heterocyclic ring-closure reactions. 3. 5-aminoimidazoles from azomethines.

Authors:  S C Mutha; R Ketcham
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7.  1-Aryl-4,6-diamino-1,2-dihydrotriazine as antimalarial agent: a new synthetic route.

Authors:  M Kidwai; P Mothsra; R Mohan; S Biswas
Journal:  Bioorg Med Chem Lett       Date:  2005-02-15       Impact factor: 2.823

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Authors:  Steven Gunawan; Joachim Petit; Christopher Hulme
Journal:  ACS Comb Sci       Date:  2012-02-15       Impact factor: 3.784

9.  Synthesis and antiviral activities of N-9-oxypurine 1,3-dioxolane and 1,3-oxathiolane nucleosides.

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10.  Efficient three-component Strecker reaction of aldehydes/ketones via NHC-amidate palladium(II) complex catalysis.

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Journal:  J Org Chem       Date:  2009-04-03       Impact factor: 4.354

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  1 in total

Review 1.  Groebke-Blackburn-Bienaymé multicomponent reaction: emerging chemistry for drug discovery.

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  1 in total

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