An Efficient Synthetic Route for Pyrrolizinone Synthesis through Functionalized C-Alkylpyrroles

Abstract

Regioselective addition of pyrrole to methyl 3-aryl-2-cyanoacrylates was achieved, in high yields, with copper(II) triflate as the catalyst in toluene. C-Alkylated pyrroles afforded novel pyrrolizin-3-ones, in good to high yields and high diastereomeric ratio by an intramolecular cyclization reaction under mild reaction conditions.

pyrrole - pyrrolizine - cyclizations - Michael additions - metal triflates

References

<A NAME="RT01509SS-1A">1a</A> Ulbrich H. Fiebich B. Dannhardt G. Eur. J. Org. Chem.  2002,  37:  953 

<A NAME="RT01509SS-1B">1b</A> Singh VP. Patil CS. Kulkarni SK. Fundam. Clin. Pharmacol.  2006,  20:  65 

<A NAME="RT01509SS-1C">1c</A> Bias P. Buchner A. Klesser B. Laufer S. Am. J. Gastroenterol.  2004,  99:  611 

<A NAME="RT01509SS-1D">1d</A> Sonnet P. Dallemagne P. Guillon J. Enguehard C. Stiebing S. Tanguy J. Bureau R. Rault S. Auvray P. Moslemi S. Sourdaine P. Seralini G.-E. Bioorg. Med. Chem.  2000,  8:  945 

<A NAME="RT01509SS-1E">1e</A> Atwell GJ. Fan J.-Y. Tan K. Denny WA. J. Med. Chem.  1998,  41:  4744 

<A NAME="RT01509SS-2">2</A> Flitsch W. Neumann U. Chem. Ber.  1971,  104:  2170 

<A NAME="RT01509SS-3">3</A> Herz W. Dittmer K. Cristol SJ. J. Am. Chem. Soc.  1948,  70:  504 

<A NAME="RT01509SS-4">4</A> McNab H. J. Org. Chem.  1981,  46:  2809 

<A NAME="RT01509SS-5A">5a</A> Pinho e Melo TMVD. Soares MIL. d’A. Rocha Gonsalves AM. Paixao JA. Beja AM. Silva MR. J. Org. Chem.  2005,  70:  6629 

<A NAME="RT01509SS-5B">5b</A> Pinho e Melo TMVD. Soares MIL. Nunes CM. Tetrahedron  2007,  63:  1833 

<A NAME="RT01509SS-6">6</A> Evans DA. Fandrick KR. Org. Lett.  2006,  8:  2249 

<A NAME="RT01509SS-7">7</A> Byers JH. DeWitt A. Nasveschuk CG. Swigor JE. Tetrahedron Lett.  2004,  45:  6587 

<A NAME="RT01509SS-8A">8a</A> Unaleroglu C. Temelli B. Demir AS. Synthesis  2004,  2574 

<A NAME="RT01509SS-8B">8b</A> Tasgin DI. Temelli B. Yazici A. Aytac S. Unaleroglu C. Lett. Org. Chem.  2008,  5:  165 

<A NAME="RT01509SS-9">9</A> Unaleroglu C. Yazici A. Tetrahedron  2007,  63:  5608 

<A NAME="RT01509SS-10">10</A> Unaleroglu C. Aytac S. Temelli B. Heterocycles  2007,  71:  2427 

<A NAME="RT01509SS-11A">11a</A> Kobayashi S. Synlett  1994,  689 

<A NAME="RT01509SS-11B">11b</A> Kobayashi S. Sugiura M. Kitagawa H. Lam WW.-L. Chem. Rev.  2002,  102:  2227 

<A NAME="RT01509SS-11C">11c</A> Luo S. Zhu L. Talukdar A. Zhang G. Mi X. Cheng J.-P. Wang PG. Mini-Rev. Org. Chem.  2005,  2:  177