Literature DB >> 14986953

Hetero Diels-Alder reactions of nitrosoamidines: an efficient method for the synthesis of functionalized guanidines.

Craig A Miller1, Robert A Batey.   

Abstract

Hetero Diels-Alder reactions of transient nitrosoamidines are reported. Transient nitrosoamidines are formed by oxidation of protected N-hydroxylguanidines and are trapped in situ by 1,3-dienes to give [4 + 2] cycloadducts in good yields and regioselectivity. The resultant cycloadducts are versatile intermediates for the formation of functionalized guanidines. [reaction: see text]

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Year:  2004        PMID: 14986953     DOI: 10.1021/ol0363117

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

1.  Metal nitrite: a powerful oxidizing reagent.

Authors:  Mahiuddin Baidya; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2011-08-16       Impact factor: 15.419

2.  Catalytic asymmetric nitroso-Diels-Alder reaction with acyclic dienes.

Authors:  Yuhei Yamamoto; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2005-11-04       Impact factor: 15.336

3.  Intramolecular [1 + 4 + 1] cycloaddition: establishment of the method.

Authors:  Douglass F Taber; Pengfei Guo; Na Guo
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

Review 4.  The nitrosocarbonyl hetero-Diels-Alder reaction as a useful tool for organic syntheses.

Authors:  Brian S Bodnar; Marvin J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-21       Impact factor: 15.336

5.  Reactions of nitroso hetero-Diels-Alder cycloadducts with azides: stereoselective formation of triazolines and aziridines.

Authors:  Brian S Bodnar; Marvin J Miller
Journal:  J Org Chem       Date:  2007-04-13       Impact factor: 4.354

6.  Diels-Alder cycloadditions in water for the straightforward preparation of peptide-oligonucleotide conjugates.

Authors:  Vicente Marchán; Samuel Ortega; Daniel Pulido; Enrique Pedroso; Anna Grandas
Journal:  Nucleic Acids Res       Date:  2006-02-14       Impact factor: 16.971

  6 in total

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