Literature DB >> 29681663

Exploring hydroamination-cycloaddition-fragmentation sequences to access polycyclicguanidines and vinyl-2-aminoimidazoles.

Ki-Hyeok Kwon1, Anne V Edwards1, Miao Yang1, Ryan E Looper1.   

Abstract

The intramolecular hydroamination of a guanidine on an eneyne unit affords a guanidine-substituted diene capable of reacting with dienophiles. These substrates undergo [4+2]-cycloaddition reactions to generate a series of complex cyclic- and spirocyclic-guanidines. Select substrates can further undergo a ring opening-elimination cascade that ultimately reveals a vinyl-2-aminoimidazole. As such this cascade reaction may find application in the synthesis of oroidin-type natural products and their analogues.

Entities:  

Keywords:  2-aminoimidazoles; Alkaloids; Cycloaddition; Heterocycle; Hydroamination

Year:  2017        PMID： 29681663      PMCID： PMC5906054          DOI： 10.1016/j.tet.2017.08.052

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


  9 in total

1.  Copper-catalyzed aerobic oxidation of hydroxamic acids leads to a mild and versatile acylnitroso ene reaction.

Authors:  Charles P Frazier; Jarred R Engelking; Javier Read de Alaniz
Journal:  J Am Chem Soc       Date:  2011-06-16       Impact factor: 15.419

2.  Direct access to marine pyrrole-2-aminoimidazoles, oroidin, and derivatives, via new acyl-1,2-dihydropyridin intermediates.

Authors:  Cosima Schroif-Gregoire; Nathalie Travert; Anne Zaparucha; Ali Al-Mourabit
Journal:  Org Lett       Date:  2006-07-06       Impact factor: 6.005

3.  Copper(II)-catalyzed room temperature aerobic oxidation of hydroxamic acids and hydrazides to acyl-nitroso and azo intermediates, and their Diels-Alder trapping.

Authors:  Duangduan Chaiyaveij; Leah Cleary; Andrei S Batsanov; Todd B Marder; Kenneth J Shea; Andrew Whiting
Journal:  Org Lett       Date:  2011-06-06       Impact factor: 6.005

4.  Regioselective rhodium(II)-catalyzed hydroaminations of propargylguanidines.

Authors:  Morgan J Gainer; Nitasha R Bennett; Yu Takahashi; Ryan E Looper
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-09       Impact factor: 15.336

5.  Copper-catalyzed aerobic oxidation of N-substituted hydroxylamines: efficient and practical access to nitroso compounds.

Authors:  Charles P Frazier; Alejandro Bugarin; Jarred R Engelking; Javier Read de Alaniz
Journal:  Org Lett       Date:  2012-07-11       Impact factor: 6.005

6.  N-substituted 2-aminoimidazole inhibitors of MRSA biofilm formation accessed through direct 1,3-bis(tert-butoxycarbonyl)guanidine cyclization.

Authors:  Andrew A Yeagley; Zhaoming Su; Kára D McCullough; Roberta J Worthington; Christian Melander
Journal:  Org Biomol Chem       Date:  2013-01-07       Impact factor: 3.876

7.  Potent small-molecule suppression of oxacillin resistance in methicillin-resistant Staphylococcus aureus.

Authors:  Tyler L Harris; Roberta J Worthington; Christian Melander
Journal:  Angew Chem Int Ed Engl       Date:  2012-10-09       Impact factor: 15.336

Review 8.  Dimeric pyrrole-imidazole alkaloids: synthetic approaches and biosynthetic hypotheses.

Authors:  Xiao Wang; Zhiqiang Ma; Xiaolei Wang; Saptarshi De; Yuyong Ma; Chuo Chen
Journal:  Chem Commun (Camb)       Date:  2014-05-15       Impact factor: 6.222

Review 9.  A submarine journey: the pyrrole-imidazole alkaloids.

Authors:  Barbara Forte; Beatrice Malgesini; Claudia Piutti; Francesca Quartieri; Alessandra Scolaro; Gianluca Papeo
Journal:  Mar Drugs       Date:  2009-11-27       Impact factor: 5.118
  9 in total

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