Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2013; 45(2): 193-198
DOI: 10.1055/s-0032-1317894
DOI: 10.1055/s-0032-1317894
paper
Michael Addition of N-Heteroaromatics to Vinylphosphonates and Synthesis of Phosphoryl Pyrrolizones by Cyclization of Michael Adducts
Further Information
Publication History
Received: 19 October 2012
Received after revision: 22 November 2012
Publication Date:
07 December 2012 (online)
Abstract
Novel phosphonate compounds were synthesized via Michael addition of N-heteroaromatic compounds to aryl- and alkyl-substituted vinylphosphonates using scandium triflate as the catalyst. Intramolecular cyclization reaction of the Michael adducts obtained gives novel (dimethoxyphosphoryl)pyrrolizin-3-ones in high yields as a single diastereomer.
Key words
phosphonates - pyrrolizinones - Michael addition - metal triflates - heteroaromatic compoundsSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Engel R. Chem. Rev. 1977; 77: 349
- 1b Moonen K, Laureyn I, Stevens CV. Chem. Rev. 2004; 104: 6177
- 1c Westheimer FH. Science (Washington, D.C.) 1987; 235: 1173
- 1d Kafarski P, Lejczak B. Phosphorus, Sulfur Silicon Relat. Elem. 1991; 63: 193
- 1e Fields SC. Tetrahedron 1999; 55: 12237
- 2a Barluenga J, Tomas M, Kouznetsov V, Suarez-Sobrino A, Rubio E. J. Org. Chem. 1996; 61: 2185
- 2b Kalantari M, Islami MR, Hassani Z, Saidi K. ARKIVOC 2006; (x): 55
- 3a Yu Z.-H, Shi D.-Q. Phosphorus, Sulfur Silicon Relat. Elem. 2010; 185: 1746
- 3b Mukherjee S, Huang C, Guerra F, Wang K, Oldfield E. J. Am. Chem. Soc. 2009; 131: 8374
- 3c Shidlovskii AF, Peregudov AS, Bulychev YN, Chkanikov ND. Pharm. Chem. J. 2009; 43: 549
- 3d Peng A.-Y, Guo Y.-J, Ke Z.-H, Zhu S. Eur. J. Org. Chem. 2008; 5277
- 4a Pham TS, Czirok JB, Balazs L, Pal K, Kubinyi M, Bitter I. Tetrahedron: Asymmetry 2011; 22: 480
- 4b Hu K, Liu T, Lu AD, Liu Y, Wang Y, Wu G, Zhou Z, Tang C. Eur. J. Org. Chem. 2011; 3507
- 4c Janecki T, Kedzia J, Wasek T. Synthesis 2009; 1227
- 4d Minami T, Nakayama M, Fujimoto K, Matsuo S. Phosphorus, Sulfur Silicon Relat. Elem. 1993; 75: 135
- 4e Minami T, Nakayama M, Fujimoto K, Matsuo S. J. Chem. Soc., Chem. Commun. 1992; 190
- 4f Inoue S, Okauchi T, Minami T. Synthesis 2003; 1971
- 4g Krawczyk H, Albrecht L, Wojciechowski J, Wolf WM. Tetrahedron 2006; 62: 9135
- 4h Blaszcyk E, Krawczyk H, Janecki T. Synlett 2004; 2685
- 4i Krawczyk H, Sliwinski M. Synthesis 2002; 1351
- 4j Couthon-Gourves H, Simon G, Haelters J.-P, Corbel B. Synthesis 2006; 81
- 5a Palacios F, Alonso C, de los Santos JM. Chem. Rev. 2005; 105: 899
- 5b Rodrigues JM, DaCosta JB. N. Phosphorus, Sulfur Silicon Relat. Elem. 2002; 177: 137
- 5c Eymery F, Iorga B, Savignac P. Tetrahedron 1999; 55: 13109
- 5d Ciszewski GM, Jackson JA. Org. Prep. Proced. Int. 1999; 31: 240
- 5e Gali H, Prabhu KR, Karra SR, Katti KV. J. Org. Chem. 2000; 65: 676
- 5f Souzy R, Ameduri B, Boutevin B, Virieux D. J. Fluorine Chem. 2004; 125: 1317
- 5g Rajeshwaran GG, Nandakumar M, Sureshbabu R, Mohanakrishnan AK. Org. Lett. 2011; 13: 1270
- 5h Cohen RJ, Fox DL, Eubank JF, Salvatore RN. Tetrahedron Lett. 2003; 44: 8617
- 6a Vicario J, Araricio D, Palacios F. J. Org. Chem. 2009; 74: 452
- 6b Matveeva EV, Shipov AE, Odinets IL. Phosphorus, Sulfur, Silicon Relat. Elem. 2011; 186: 698
- 7a Sobenina LN, Drichkov VN, Mikhaleva AI, Petrova OV, Ushakov IA, Trofimov BA. ARKIVOC 2005; (vii): 28
- 7b 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
- 9a Yavari I, Djahaniani H, Maghsoodlou MT, Hazeri N. J. Chem. Res., Synop. 1999; 382
- 9b Pinho e Melo TM. V. D, Soares MI. L, Nunes CM. Tetrahedron 2007; 63: 1833
- 10 Unaleroglu C, Tasgin DI, Aytac S, Temelli B. Synthesis 2009; 3243
- 11a McNab H. J. Org. Chem. 1981; 46: 2809
- 11b McNab H, Reed D, Tipping ID, Tyas RG. ARKIVOC 2007; (xi): 85
- 11c Mallik AK, Dey SP, Chattopadhyay F, Patra A. Tetrahedron Lett. 2002; 43: 1295
- 11d Byers HB, DeWitt A, Nasveschuk CG, Swigor JE. Tetrahedron Lett. 2004; 45: 6587
- 12a Unaleroglu C, Temelli B, Demir AS. Synthesis 2004; 2574
- 12b Unaleroglu C, Yazici A. Tetrahedron 2007; 63: 5608
- 12c Unaleroglu C, Aytac S, Temelli B. Heterocycles 2007; 71: 2427
- 12d Tasgin DI, Temelli B, Yazici A, Aytac S, Unaleroglu C. Lett. Org. Chem. 2008; 5: 165
- 13 Patai S, Schwartz A. J. Org. Chem. 1960; 25: 1232
- 14 Nickson TE. J. Org. Chem. 1988; 53: 3870
- 15a Chiba R, Oriyama T. Chem. Lett. 2008; 37: 1218
- 15b Snider BB, Philips GB. J. Org. Chem. 1983; 48: 3685
- 16 Chiefari J, Galanopoulos S, Janowski WK, Kerr DI. B, Prager RH. Aust. J. Chem. 1987; 40: 1511