Synlett, Inhaltsverzeichnis Synlett 2013; 24(7): 865-867DOI: 10.1055/s-0032-1318487 letter © Georg Thieme Verlag Stuttgart · New YorkTriflic Acid Mediated Fries Rearrangement of 3-Dienyl-2-azetidinones: Facile Synthesis of 3-(But-2-enylidene)quinolin-4(3H)-ones Amit Anand Department of Chemistry, Guru Nanak Dev University, Amritsar 143005, India Fax: +91(183)225881920 eMail: vipan_org@yahoo.com , Vishu Mehra Department of Chemistry, Guru Nanak Dev University, Amritsar 143005, India Fax: +91(183)225881920 eMail: vipan_org@yahoo.com , Vipan Kumar* Department of Chemistry, Guru Nanak Dev University, Amritsar 143005, India Fax: +91(183)225881920 eMail: vipan_org@yahoo.com› InstitutsangabenArtikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract β-Lactam-synthon-interceded synthesis of 3-(but-2-enylidene)quinolin-4(3H)-ones has been described via triflic acid mediated Fries rearrangement of 3-butadienyl-2-azetidinones. The described protocol provides a direct access to C-3 functionalized quinolin-4(3H)-ones and does not suffer from the disadvantages associated with conventional routes. Key words Key words3-dienyl-β-lactam - triflic acid - Fries rearrangement - quinolin-4(3H)-one - β-lactam synthon protocol Volltext Referenzen References and Notes 1 Emami S, Foroumadi A, Samadi N, Faramarzi MA, Rajabalian S. Arch. Pharm. (Weinheim, Ger.) 2009; 342: 405 2 Bridges AJ, Moos WH, Szotek DL, Trivedi BK, Bristol JA, Heffner TG, Bruns RF, Downs DA. J. Med. Chem. 1987; 30: 1711 3 Jarak I, Kralj M, Piantanida I, Šuman L, Zinić M, Pavelić K, Karminski-Zamola G. Bioorg. Med. Chem. 2006; 14: 2859 4 Ogata M, Matsumoto H, Hirose K. J. Med. Chem. 1977; 20: 776 5 Cross RM, Monastyrskyi A, Mutka TS, Burrows JN, Kyle DE, Manetsch R. J. Med. Chem. 2010; 53: 7076 6a Sato M, Motomura T, Aramaki H, Matsuda T, Yamashita M, Ito Y, Kawakami H, Matsuzaki Y, Watanabe W, Yamataka K, Ikeda S, Kodama E, Matsuoka M, Shinkai H. J. 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IR (KBr): 1627, 1684 cm–1. 1H NMR (300 MHz, CDCl3): δ = 1.86 (d, J = 5.4 Hz, 3 H, CH3), 5.88 (d, 1 H, J = 15.0 Hz, H2), 6.17 (m, 2 H, H1 and H3), 7.10 (t, 1 H, J = 7.5 Hz, ArH), 7.26–7.36 (m, 6 H, ArH), 7.54–7.57 (m, 2 H, ArH). 13C NMR (75 MHz, CDCl3): δ = 19.5, 127.0, 127.1, 127.7, 128.2, 128.8, 129.2, 130.2, 130.4, 131.0, 131.2, 135.8, 138.9, 143.1, 153.5, 164.8, 177.4. ESI-MS: m/z = 273 [M]+. Anal. Calcd for C19H15NO: C, 83.49; H, 5.53; N, 5.12. Found: C, 83.57; H, 5.65; N, 5.02. 3-(But-2-enylidene)-2-p-tolylquinolin-4(3H)-one (2b) Pale yellow solid; mp 96–97 °C. IR (KBr): 1627, 1685 cm–1. 1H NMR (300 MHz, CDCl3): δ = 1.88 (d, J = 5.4 Hz, 3 H, CH3), 2.25 (s, 3 H, CH3C6H4), 5.86 (d, 1 H, J = 15.0 Hz, H2), 6.16 (m, 2 H, H1 and H3), 7.12 (t, 1 H, J = 7.5 Hz, ArH), 7.30–7.42 (m, 5 H, ArH), 7.57–7.61 (m, 2 H, ArH). 13C NMR (75 MHz, CDCl3): δ = 19.6, 21.5, 127.0, 127.2, 127.8, 128.3, 129.0, 129.2, 130.2, 130.5, 131.2, 135.8, 136.6, 140.3, 143.3, 153.2, 164.6, 177.2. ESI-MS: m/z = 287 [M]+. Anal. Calcd for C20H17NO: C, 83.59; H, 5.96; N, 4.87. Found: C, 83.74; H, 6.06; N, 4.72.
