Copper(I)-Promoted Regioselective α-Tricyanoethenylation
of N-Methylpyrroles

Vladislav N. Drichkov; Lyubov’ N. Sobenina; Tamara I. Vakul’skaya; Igor’ A. Ushakov; Al’bina I. Mikhaleva; Boris A. Trofimov

doi:10.1055/s-2008-1067178

PAPER

Copper(I)-Promoted Regioselective α-Tricyanoethenylation of N-Methylpyrroles

Vladislav N. Drichkov, Lyubov’ N. Sobenina, Tamara I. Vakul’skaya, Igor’ A. Ushakov, Al’bina I. Mikhaleva, Boris A. Trofimov*
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russian Federation
Fax: +7(3952)419346; e-Mail: boris_trofimov@irioch.irk.ru;

Abstract

All articles of this category

Abstract

The reaction of N-methylpyrroles with tetracyanoethylene (TCNE) has been studied in various solvents (DMSO, acetone, THF). A highly efficient protocol for the copper(I)-promoted regioselective α-tricyanoethenylation of N-methylpyrroles has been developed.

Key words

N-methylpyrroles - TCNE - tricyanoethenylation - copper(I) bromide - regioselectivity

Full Text

References

<A NAME="RZ08708SS-1A">1a</A> Varanasi PR. Jen AK.-J. Chandrasekhar J. Namboothiri INN. Rathna A. J. Am. Chem. Soc. 1996, 118: 12443

<A NAME="RZ08708SS-1B">1b</A> Albert IDL. Marks TJ. Ratner MA. J. Am. Chem. Soc. 1997, 119: 6575

<A NAME="RZ08708SS-1C">1c</A> Takahashi K. Tarutani S. Chem. Commun. 1998, 1233

<A NAME="RZ08708SS-1D">1d</A> Schmitt S. Baumgarten M. Simon J. Hafner K. Angew. Chem. Int. Ed. 1998, 37: 1078

<A NAME="RZ08708SS-1E">1e</A> Suzuki T. Nishida J. Tsuji T. Chem. Commun. 1998, 1331

<A NAME="RZ08708SS-1F">1f</A> Gonzalez M. Martin N. Segura JL. Seoane C. Garin J. Ornuda J. Alcala R. Sanchez C. Villicampa B. Tetrahedron Lett. 1999, 40: 8599

<A NAME="RZ08708SS-1G">1g</A> Skabara PJ. Serebryakov IM. Perepichka IF. J. Chem. Soc., Perkin Trans. 2 1999, 505

<A NAME="RZ08708SS-1H">1h</A> Mikami S. Sugiura K. Miller JS. Sakata Y. Chem. Lett. 1999, 413

<A NAME="RZ08708SS-1I">1i</A> Kurata H. Inase M. Oda M. Chem. Lett. 1999, 519

<A NAME="RZ08708SS-1J">1j</A> Lee B.-L. Yamamoto T. Macromolecules 1999, 32: 1375

<A NAME="RZ08708SS-1K">1k</A> Hirayma D. Yamashiro T. Takimiya K. Aso Y. Otsubo T. Norieda H. Imahori H. Sakata Y. Chem. Lett. 2000, 570

<A NAME="RZ08708SS-1L">1l</A> Skaraba PJ. Serebryakov IM. Macromolecules 2001, 34: 2232

<A NAME="RZ08708SS-2">2</A> Raposo MMM. Sousa AMRC. Kirsch G. Ferreira F. Belsley M. Gomes EM. Fonseca AMC. Tetrahedron 2005, 61: 11991

<A NAME="RZ08708SS-3A">3a</A> Ogura K. Yanay H. Miokawa M. Akazome M. Tetrahedron Lett. 1999, 40: 8887

<A NAME="RZ08708SS-3B">3b</A> Zhao R. Akazome M. Matsumoto S. Ogura K. Tetrahedron 2002, 58: 10225

<A NAME="RZ08708SS-3C">3c</A> Zhao R. Akazome M. Matsumoto S. Ogura K. Bull. Chem. Soc. Jpn. 2002, 75: 2359

<A NAME="RZ08708SS-3D">3d</A> Ogura K. Zhao R. Jiang M. Akazome M. Matsumoto S. Yamaguchi K. Tetrahedron Lett. 2003, 44: 3595

<A NAME="RZ08708SS-3E">3e</A> Eckert K. Schroder A. Hartmann H. Eur. J. Org. Chem. 2000, 1327

<A NAME="RZ08708SS-4">4</A> Trofimov BA. Sobenina LN. Demenev AP. Mikhaleva AI. Ushakov IA. Tarasova OA. Smirnov VI. Petrushenko KB. Vokin AI. Murzina NM. Myachina GF. ARKIVOC 2001, (ix): 37

<A NAME="RZ08708SS-5A">5a</A> Sausen GN. Engelhardt VA. Middleton WJ. J. Am. Chem. Soc. 1958, 80: 2815

<A NAME="RZ08708SS-5B">5b</A> McCormac T. Farrell D. Electrochim. Acta 2001, 46: 3287

<A NAME="RZ08708SS-6">6</A> Vokin AI. Vakul’skaya TI. Murzina NM. Demenev AP. Sobenina LN. Mikhaleva AI. Trofimov BA. Russ. J. Org. Chem. 2000, 36: 1504

<A NAME="RZ08708SS-7">7</A> Miller JS. Angew. Chem. Int. Ed. 2006, 45: 2508

<A NAME="RZ08708SS-8">8</A> Solomon EI. Sundraham UV. Machonkin TE. Chem. Rev. 1996, 96: 2563

<A NAME="RZ08708SS-9">9</A> Heaney H. Ley SV. J. Chem. Soc., Perkin Trans. 1 1973, 499