Cycloaddition Reactions of N-Benzotriazolylketene as a Heteroarylketene: A Practical Approach to the Synthesis of Novel Azetidinones

Abstract

A series of novel functionalized azetidinones containing the benzotriazole moiety were synthesized stereoselectively by a ­reaction of benzotriazolylacetic acid, aromatic amines, and ­Mukaiyama’s reagent in the presence of triethylamine in dichloromethane at ambient temperature. This transformation generates a four-membered lactam and presumably proceeds via in situ generation of benzotriazolylketene as a heteroarylketene. In contrast to the products obtained from the reaction of pyrrolylketene with imines in which cis-azetidinones were formed as major products, the generated benzotriazolylyketene reacted with imines forming the trans-lactams as major products.

Key words

ketenes - Schiff bases - N-benzotriazolylketene - [2π+2π] cycloaddition - azetidinones

• References

• 1 Elander RP. Appl. Microbiol. Biotechnol. 2003; 61: 385
• 2 Pichichero ME. Pediatrics 2005; 115: 1048
• 3 Fisher JF, Meroueh SO, Mobashery S. Chem. Rev. 2005; 105: 395
• 4 Kasten B, Reski R. J. Plant Physiol. 1997; 150: 137
• 5 Nangia A, Biradha K, Desiraju GR. J. Chem. Soc., Perkin Trans. 2 1996; 943
• 6 Cohen NC. J. Med. Chem. 1983; 26: 259
• 7 O’Boyle NM, Carr M, Greene LM, Bergin O, Nathwani SM, McCabe T, Lloyd DG, Zisterer DM, Meegan MJ. J. Med. Chem. 2010; 53: 8569
• 8 O’Boyle NM, Greene LM, Bergin O, Jean-Baptiste F, McCabe T, Lloyd DG, Zisterer DM, Meegan MJ. Bioorg. Med. Chem. 2011; 19: 2306
• 9 Hengzhuang W, Ciofu O, Yang L, Wu H, Song Z, Oliver A, Høiby N. Antimicrob. Agents Chemother. 2013; 57: 196
• 10 Herzberg O, Moult J. Science 1987; 236: 694
• 11 Nichol KA, Zhanel GG, Hoban DJ. Antimicrob. Agents Chemother. 2002; 46: 3261
• 12 Tipper DJ. Rev. Infect. Dis. 1979; 1: 39
• 13 Staudinger H. Justus Liebigs Ann. Chem. 1907; 356: 51
• 14 Islami MR, Allen AD, Vukovic S, Tidwell TT. Org. Lett. 2011; 13: 494
• 15 Jiao L, Liang Y, Xu J. J. Am. Chem. Soc. 2006; 128: 6060
• 16 Lee SH. Bull. Korean Chem. Soc. 2013; 34: 121
• 17 Tidwell TT. Angew. Chem. Int. Ed. 2008; 47: 1016
• 18 Leung-Toung R, Tidwell TT. J. Am. Chem. Soc. 1990; 112: 1042
• 19 Sharma AK, Mahajan MP. Tetrahedron 1997; 53: 13841
• 20 Bandyopadhyay D, Cruz J, Banik BK. Tetrahedron 2012; 68: 10686
• 21 Liu R, Tidwell TT. Can. J. Chem. 1995; 73: 1818
• 22 Allen AD, Tidwell TT. Eur. J. Org. Chem. 2012; 1081
• 23 Penn JH, Owens WH. J. Am. Chem. Soc. 1993; 115: 82
• 24 Baigrie LM, Seikaly HR, Tidwell TT. J. Am. Chem. Soc. 1985; 107: 5391
• 25 Leung-Toung R, Wentrup C. J. Org. Chem. 1992; 57: 4850
• 26 Alonso E, Lόpez-Ortiz F, del Pozo C, Peralta E, Macίas A, González J. J. Org. Chem. 2001; 66: 6333
• 27 Bennett DM, Okamoto I, Danheiser RL. Org. Lett. 1999; 1: 641
• 28 Brady WT, Saidi K. J. Org. Chem. 1979; 44: 733
• 29 Montaigne R, Ghosez L. Angew. Chem., Int. Ed. Engl. 1968; 7: 221
• 30 Brady WT, Saidi K. J. Org. Chem. 1980; 45: 727
• 31 Katritzky AR, Wu J, Kuzmierkiewicz W, Rachwal S. Liebigs Ann. Chem. 1994; 1
• 32 Eugene DR, Vernon KR. US 4,240,822, 1980
• 33 Eugene DR, Vernon KR. US 4,086,242, 1978
• 34 Suma BV, Natesh NN, Madhavan V. J. Chem. Pharm. Res. 2011; 3: 375
• 35 Sanna P, Carta A, Rahbar Nikookar ME. Eur. J. Med. Chem. 2000; 35: 535
• 36 Sharma SD, Saluja A, Bhaduri S. Indian J. Chem., Sect. B.: Org. Chem. Incl. Med. Chem. 2000; 39: 156
• 37 Sheibani H, Islami MR, Khabazzadeh H, Saidi K. Tetrahedron 2004; 60: 5931
• 38 Pellicciari R, Fringuelli R, Natalini B, Brucato L, Contessa AR. Arch. Pharm. 1985; 318: 393
• 39 Gupton JT, Hicks FA, Smith SQ, Main AD, Petrich SA, Wilkinson DR, Sikorski JA, Katritzky AR. Tetrahedron 1993; 49: 10205
• 40 Khalafi-Nezhad A, Zare A, Parhami A, Soltani Rad MN, Nejabat GR. J. Iran. Chem. Soc. 2007; 4: 271
• 41 Fu N, Tidwell TT. Tetrahedron 2008; 64: 10465
• 42 Cossio FP, Ugalde JM, Lopez X, Lecea B, Palomo C. J. Am. Chem. Soc. 1993; 115: 995