Novel, Efficient and Regiospecific Alkylation/Arylation/Heteroarylation of Unsymmetrical Azo Compounds

Olga Tšubrik; Rannar Sillard; Uno Mäeorg

doi:10.1055/s-2006-926331

PAPER

Novel, Efficient and Regiospecific Alkylation/Arylation/Heteroarylation of Unsymmetrical Azo Compounds

Olga Tšubrik^a, Rannar Sillard^b, Uno Mäeorg*^a
^a Institute of Organic and Bioorganic Chemistry, University of Tartu, Jakobi 2, 51014 Tartu, Estonia
^b Department of Medical Biochemistry and Biophysics, Karolinska Institutet, 171-77 Stockholm, Sweden
Fax: +372(7)375245; e-Mail: uno.maeorg@ut.ee;

Abstract

All articles of this category

Abstract

Excellent regioselectivity is observed in the addition of diverse organometallic nucleophiles to unsymmetrical azo compounds. Primary/secondary/tertiary alkyl, aryl and heteroaryl substituents were introduced this way in high yields.

Key words

azo compounds - hydrazines - regioselectivity - neighboring group effects - protecting groups

Full Text

References

<A NAME="RZ16605SS-1">1</A> Vilme M. Edwards D. McPherson-Baker S. Drug Forecast 2005, 30: 27

<A NAME="RZ16605SS-2">2</A> For a review, see: Ragnarsson U. Chem. Soc. Rev. 2001, 30: 205 ; and references cited therein

<A NAME="RZ16605SS-3A">3a</A> Mäeorg U. Grehn L. Ragnarsson U. Angew. Chem., Int. Ed. Engl. 1996, 35: 2626

<A NAME="RZ16605SS-3B">3b</A> Tšubrik O. Mäeorg U. Org. Lett. 2001, 3: 2297

<A NAME="RZ16605SS-3C">3c</A> Brosse N. Jamart-Gregoire B. Tetrahedron Lett. 2002, 43: 249

<A NAME="RZ16605SS-3D">3d</A> Brosse N. Pinto M.-F. Jamart-Grégoire B. J. Org. Chem. 2000, 65: 4370

<A NAME="RZ16605SS-3E">3e</A> Ragnarsson U. Grehn L. Koppel J. Loog O. Tšubrik O. Bredikhin A. Mäeorg U. Koppel I. J. Org. Chem. 2005, 70: 5916

<A NAME="RZ16605SS-3F">3f</A> Bredikhin A. Tšubrik O. Sillard R. Mäeorg U. Synlett 2005, 1939

<A NAME="RZ16605SS-4A">4a</A> Mauger C. Mignani G. Adv. Synth. Catal. 2005, 347: 773

<A NAME="RZ16605SS-4B">4b</A> Tšubrik O. Mäeorg U. Sillard R. Ragnarsson U. Tetrahedron 2004, 60: 8363

<A NAME="RZ16605SS-4C">4c</A> Loog O . Mäeorg U . Synlett 2004, 2537

<A NAME="RZ16605SS-4D">4d</A> Tšubrik O. Mäeorg U. Ragnarsson U. Tetrahedron Lett. 2002, 43: 6213

<A NAME="RZ16605SS-4E">4e</A> Wolter M. Klapars A. Buchwald SL. Org. Lett. 2001, 3: 3803

<A NAME="RZ16605SS-4F">4f</A> Arterburn JB. Rao KV. Ramdas R. Dible BR. Org. Lett. 2001, 3: 1351

<A NAME="RZ16605SS-5A">5a</A> List B. J. Am. Chem. Soc. 2002, 124: 5656

<A NAME="RZ16605SS-5B">5b</A> Velardo-Ortiz R. Guijarro A. Rieke RD. Tetrahedron Lett. 1998, 39: 9157

<A NAME="RZ16605SS-5C">5c</A> Bombek S. Po˛gan F. Koèevar M. Polanc S. J. Org. Chem. 2004, 69: 2224

<A NAME="RZ16605SS-5D">5d</A> Leblanc Y. Boudreault N. J. Org. Chem. 1995, 60: 4268

<A NAME="RZ16605SS-6">6</A> Evans DA. Johnson DS. Org. Lett. 1999, 1: 595

<A NAME="RZ16605SS-7">7</A> Sapountzis I. Knochel P. Angew. Chem. Int. Ed. 2004, 43: 897

<A NAME="RZ16605SS-8">8</A> Starr JT. Rai GS. Dang H. McNelis BJ. Synth. Commun. 1997, 27: 3197

<A NAME="RZ16605SS-9">9</A> Trecourt F. Breton G. Bonnet V. Mongin F. Marsais F. Queginer G. Tetrahedron 2000, 56: 1349