Synlett, Inhaltsverzeichnis Synlett 2013; 24(15): 1937-1940DOI: 10.1055/s-0033-1339520 letter © Georg Thieme Verlag Stuttgart · New York Stereoselective Synthesis of New β-Lactams from 2-(1H-Pyrrol-1-yl)-1-propen-1-one as a Novel Ketene Elaheh Babaei a Department of Chemistry, Shahid Bahonar University, 76169 Kerman, Iran Fax: +98(341)3222033 eMail: mrislami@uk.ac.ir , Mohammad Reza Islami* a Department of Chemistry, Shahid Bahonar University, 76169 Kerman, Iran Fax: +98(341)3222033 eMail: mrislami@uk.ac.ir , Maryam Kalantari b Department of Chemical engineering, Shahid Bahonar University, 76169 Kerman, Iran › Institutsangaben Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract New trans-β-lactams have been stereoselectively prepared by the reaction of N-pyrrolylpropanoic acid with 2-chloro-1-methylpyridinium iodide and aromatic imines in the presence of triethylamine as a base via in situ generation of methyl-2-(1H-pyrrol-1-yl)ketene as a novel heteroarylketene. The trans-β-lactam was formed either as a single isomer or as the major isomer. Key words Key wordsketenes - imines - N-pyrrolylpropanoic acid - [2π + 2π] cycloaddition - β-lactams Volltext Referenzen References 1 Leung-Toung R, Tidwell TT. J. Am. Chem. Soc. 1990; 112: 1042 2 Tsuda T, Hokazono H, Toyota K. J. Chem. Soc., Chem. Commun. 1995; 2417 3 Sharma AK, Mahajan MP. Tetrahedron 1997; 53: 13841 4 Bandyopadhyay D, Cruz J, Banik BK. Tetrahedron 2012; 68: 10686 5 Liu R, Tidwell TT. Can. J. Chem. 1995; 73: 1818 6 Allen AD, Tidwell TT. Eur. J. Org. Chem. 2012; 1081 7 Staudinger H. Ber. Dtsch. Chem. Ges. 1905; 38: 1735 8 Duckworth AC. J. Org. Chem. 1962; 27: 3146 9 Penn JH, Owens WH. J. Am. Chem. Soc. 1993; 115: 82 10 Baigrie LM, Seikaly HR, Tidwell TT. J. Am. Chem. Soc. 1985; 107: 5391 11 Leung-Toung R, Wentrup C. J. Org. Chem. 1992; 57: 4850 12 Leung-Toung R, Peterson MR, Tidwell TT, Csizmadia IG. J. Mol. Struct. 1989; 183: 319 13 Alonso G, Lόpez-Ortiz F, del Pozo C, Peralta E, Macίas A, González J. J. Org. Chem. 2001; 66: 6333 14 Bennett DM, Okamoto I, Danheiser RL. Org. Lett. 1999; 1: 641 15 Chen YP, Chantegrel B, Deshayes S. Heterocycles 1995; 41: 175 16 Matsui S, Kinbara K, Saigo K. Tetrahedron Lett. 1999; 40: 899 17 Brady WT, Saidi K. J. Org. Chem. 1979; 44: 733 18 Bittner J, Seppelt K. Chem. Ber. 1990; 123: 2187 19 Montaigne R, Ghosez L. Angew. Chem., Int. Ed. Engl. 1968; 7: 221 20 Brady WT, Saidi K. J. Org. Chem. 1980; 45: 727 21 Arya F, Bouquant J, Chuche J. Tetrahedron Lett. 1986; 27: 1913 22 Brady WT, Gu Y. J. Org. Chem. 1988; 53: 1353 23 France S, Wack H, Taggi AE, Hafez AM, Wagerle TR, Shah MH, Dusich CL, Lectka T. J. Am. Chem. Soc. 2004; 126: 4245 24 Bacchi S, Bongini A, Panunzio M, Villa M. Synlett 1998; 843 25 Müller M, Birner G, Dekant W. Chem. Res. Toxicol. 1998; 11: 454 26 Palomo C, Aizpurua JM, Ganboa I, Odriozola B, Urchegui R, Görls H. Chem. Commun. 1996; 1269 27 Sheehan JC, Henery-Logan KR. J. Am. Chem. Soc. 1957; 79: 1262 28 Woodward RB, Heusler K, Gosteli J, Naegeli P, Oppolzer W, Ramage R, Ranganathan S, Vorbrüggen H. J. Am. Chem. Soc. 1966; 88: 852 29 Yerxa BR, Moore HW. Tetrahedron Lett. 1992; 33: 7811 30 Merino I, Hegedus LS. Organometallics 1995; 14: 2522 31 Islami MR, Allen AD, Vukovic S, Tidwell TT. Org. Lett. 2011; 13: 494 32 Fu N, Allen AD, Chan W, Kobayashi S, Tidwell TT, Tahmassebi D, Aguilar A, Cabrera EP, Godoy J. Can. J. Chem. 2008; 86: 333 33 Gong L, McAllister MA, Tidwell TT. J. Am. Chem. Soc. 1991; 113: 6021 34 Tidwell TT. Ketenes . 2nd ed. John Wiley; Hoboken: 2006 35 Aguilar-Aguilar A, Allen AD, Peña-Cabrera E, Fedorov A, Fu N, Henry-Riyad H, Kobayashi S, Leuninger J, Schmid U, Tidwell TT, Verma R. J. Org. Chem. 2005; 70: 9556 36a Wang D, Nanding H, Han N, Chen F, Zhao G. J. Agric. Food Chem. 2008; 56: 1495 36b Gloede J, Poduska K, Gross H, Rudinger J. Collect. Czech. Chem. Commun. 1968; 33: 1307 37 Fu N, Tidwell TT. Tetrahedron 2008; 64: 10465 38 Jiao L, Liang Y, Xu J. J. Am. Chem. Soc. 2006; 128: 6060 39 Cossio FP, Ugalde JM, Lopez X, Lecea B, Palomo C. J. Am. Chem. Soc. 1993; 115: 995 Zusatzmaterial Zusatzmaterial Supporting Information
