Regioselective Cross-Coupling of 1-Vinylpyrroles with Acylbromoacetylenes on Al2O3: Synthesis of 2-(2-Acylethynyl)-1-vinylpyrroles

B. A. Trofimov; L. N. Sobenina; Z. V. Stepanova; I. A. Ushakov; O. V. Petrova; O. A. Tarasova; K. A. Volkova; A. I. Mikhaleva

doi:10.1055/s-2007-965884

PAPER

Regioselective Cross-Coupling of 1-Vinylpyrroles with Acylbromoacetylenes on Al₂O₃: Synthesis of 2-(2-Acylethynyl)-1-vinylpyrroles

B. A. Trofimov*, L. N. Sobenina, Z. V. Stepanova, I. A. Ushakov, O. V. Petrova, O. A. Tarasova, K. A. Volkova, A. I. Mikhaleva
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, Russia
Fax: +7(3952)511926; e-Mail: boris_trofimov@irioch.irk.ru;

Abstract

All articles of this category

Abstract

1-Vinyl- and 1-isopropenylpyrroles enter readily (ambient temperature) into cross-coupling reaction with acylbromoacetylenes on Al₂O₃ to furnish regioselectively 2-(2-acylethynyl)-1-vinyl- and 2-(2-acylethynyl)-1-isopropenylpyrroles in 39-70% yield.

Key words

1-vinylpyrroles - 1-isopropenylpyrroles - acylbromoacetylenes - 2-(2-acylethynyl)pyrroles - cross-coupling reaction - Al₂O₃

Full Text

References

<A NAME="RZ15506SS-1A">1a</A> Jones RA. Pyrroles Wiley; New York: 1990. Part 2.

<A NAME="RZ15506SS-1B">1b</A> Gribble GW. In Comprehensive Heterocyclic Chemistry II Vol 2: Katritzky AR. Ress CW. Scriven EFV. Pergamon; Oxford: 1996.

<A NAME="RZ15506SS-2A">2a</A> Molander GA. Schmitt MH. J. Org. Chem. 2000, 65: 3767

<A NAME="RZ15506SS-2B">2b</A> Joseph B. Da Costa H. Merour J.-Y. Leonce S. Tetrahedron 2000, 56: 3189

<A NAME="RZ15506SS-2C">2c</A> Molina P. Fresneda PM. Delgado S. Bleda JA. Tetrahedron Lett. 2002, 43: 1005

<A NAME="RZ15506SS-2D">2d</A> Trofimov BA. Sobenina LN. Demenev AP. Mikhaleva AI. Chem. Rev. 2004, 104: 2481

<A NAME="RZ15506SS-3A">3a</A> Jones RA. Aznar-Saliente T. Sepulveda-Arques J. J. Chem. Soc., Perkin Trans. 1 1984, 2451

<A NAME="RZ15506SS-3B">3b</A> Ohno M. Shimizu S. Eguchi S. Tetrahedron Lett. 1990, 31: 4613

<A NAME="RZ15506SS-3C">3c</A> Keil JM. Kampchen T. Seitz G. Tetrahedron Lett. 1990, 31: 4581

<A NAME="RZ15506SS-3D">3d</A> Gribble GW. Contemp. Org. Synth. 1994, 1: 145

<A NAME="RZ15506SS-3E">3e</A> Hodges LM. Moody MW. Harman WD. J. Am. Chem. Soc. 1994, 116: 7931

<A NAME="RZ15506SS-4A">4a</A> Naarmann H. Theophilou N. In Electroresponsive Molecular and Polymeric Systems Vol. 1: Marcel Dekker; New York: 1988.

<A NAME="RZ15506SS-4B">4b</A> Niziurski-Mann RE. Cava MP. Heterocycles 1992, 34: 2003

<A NAME="RZ15506SS-4C">4c</A> Bauerle P. Adv. Mater. 1993, 5: 879

<A NAME="RZ15506SS-4D">4d</A> Alagona G. Ghio C. Cavazza M. Nucci L. Pergola F. Colligiani A. Synth. Met. 1994, 67: 235

<A NAME="RZ15506SS-5A">5a</A> Trofimov BA. Stepanova ZV. Sobenina LN. Mikhaleva AI. Ushakov IA. Tetrahedron Lett. 2004, 45: 6513

<A NAME="RZ15506SS-5B">5b</A> Trofimov BA. Stepanova ZV. Sobenina LN. Mikhaleva AI. Sinegovskaya LM. Potekhin KA. Fedaynin IV. Mendeleev Commun. 2005, 15: 229

<A NAME="RZ15506SS-6A">6a</A> Trofimov BA. Mikhaleva AI. N-Vinylpyrroles Nauka; Novosibirsk: 1984.

<A NAME="RZ15506SS-6B">6b</A> Trofimov BA. Vinylpyrroles, In Pyrroles: The Synthesis, Reactivity and Physical Properties of Substituted Pyrroles Jones A. Wiley; New York: 1992. Chap. 2.

<A NAME="RZ15506SS-7">7</A> Zhdanov YuA. Minkin VI. Correlation Analysis in Organic Chemistry Rostov University Publishers; Rostov: 1966.

<A NAME="RZ15506SS-8A">8a</A> Hania MM. Asian J. Chem. 2000, 12: 321 ; Chem. Abstr. 1999, 132, 136998

<A NAME="RZ15506SS-8B">8b</A> Yoshida T. Ito A. Ibusuki K. Murase M. Kotani E. Chem. Pharm. Bull. 2001, 49: 1198

<A NAME="RZ15506SS-9">9</A> Trofimov BA. Tarasova OA. Mikhaleva AI. Kalinina NA. Sinegovskaya LM. Henkelmann J. Synthesis 2000, 1585