Synthesis, Inhaltsverzeichnis PAPER© Georg Thieme Verlag Stuttgart · New YorkRegioselective Synthesis of Oxepin- and Oxocin-Annulated 2-QuinolonesShital K. Chattopadhyay*, Rajat Dey, Suman BiswasDepartment of Chemistry, University of Kalyani, Kalyani-741235, IndiaFax: +91(33)25828282; e-Mail: skchatto@yahoo.com; Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract A synthetic strategy based on tandem Claisen rearrangement and ring-closing metathesis was developed for the regioselective synthesis of some hitherto unknown oxepin- and oxocin-annulated 2-quinolones. Key words Claisen rearrangement - ring-closing metathesis - quinolones - oxepin - oxocin Volltext Referenzen References <A NAME="RT06804SS-1A">1a</A> Abd E. Hisham A. Pharmazie 1997, 52: 28 <A NAME="RT06804SS-1B">1b</A> Sun HB. Qing FL. Chen XF. Synthesis 1997, 1249 <A NAME="RT06804SS-1C">1c</A> Nevile CF. Grundon MF. Ramchandran VN. Reisch G. Reisch J. J. Chem. Soc., Perkin Trans. 1 1991, 2261 <A NAME="RT06804SS-2A">2a</A> Staubitz A. Dohle W. Knochel P. Synthesis 2003, 233 <A NAME="RT06804SS-2B">2b</A> Lee YR. Kweon HI. Koh WS. Min KR. Kim Y. Lee SH. Synthesis 2001, 1851 <A NAME="RT06804SS-2C">2c</A> Ullrich T. Girard F. Tetrahedron Lett. 2003, 44: 4207 <A NAME="RT06804SS-3A">3a</A> Yang Z.-Y. Xia Y. Xia P. Brossi A. Lee K.-H. Tetrahedron Lett. 1999, 40: 4505 <A NAME="RT06804SS-3B">3b</A> Ye J.-H. Ling K.-Q. Zhang Y. Li N. Xu J.-H. J. Chem. Soc., Perkin Trans. 1 1999, 2017 <A NAME="RT06804SS-3C">3c</A> Majumdar KC. Ghosh SK. Biswas P. Monatsh. Chem. 2000, 31: 967 <A NAME="RT06804SS-4">4</A> Yet L. Chem. Rev. 2000, 100: 2963 For recent reviews, see: <A NAME="RT06804SS-5A">5a</A> Trnka TM. Grubbs RH. Acc. Chem. Res. 2001, 34: 18 <A NAME="RT06804SS-5B">5b</A> Fürstner A. Angew. Chem. Int. Ed. 2000, 39: 3012 <A NAME="RT06804SS-5C">5c</A> Blechert S. Connon S. Angew. Chem. Int. Ed. 2003, 42: 1900 <A NAME="RT06804SS-5D">5d</A> Poulsen CS. Madsen R. Synthesis 2003, 1 For some recent applications of RCM reaction in medium ring oxacycle formation, see: <A NAME="RT06804SS-6A">6a</A> Mamouni R. Soukri M. Lazar S. Akssira M. Guillaumet G. Tetrahedron Lett. 2004, 45: 2631 <A NAME="RT06804SS-6B">6b</A> Van Otterlo WAL. Pathak R. de Koning CB. Synlett 2003, 1859 <A NAME="RT06804SS-6C">6c</A> Pain C. Celanire S. Guillaumet G. Joseph B. Synlett 2003, 2089 <A NAME="RT06804SS-7A">7a</A> Chattopadhyay SK. Maity S. Panja S. Tetrahedron Lett. 2002, 43: 7781 <A NAME="RT06804SS-7B">7b</A> Chattopadhyay SK. Paul BK. Maity S. Chem. Lett. 2003, 32: 1190 For some recent reviews on Claisen rearrangement, see: <A NAME="RT06804SS-8A">8a</A> Nubbemeyer U. Synthesis 2003, 961 <A NAME="RT06804SS-8B">8b</A> Castro AMM. Chem. Rev. 2004, 104: 2939 <A NAME="RT06804SS-8C">8c</A> Blechert S. Synthesis 1989, 71 <A NAME="RT06804SS-9">9</A> Chamberlin TR. Grundon MF. Tetrahedron Lett. 1967, 3547 <A NAME="RT06804SS-10A">10a</A> Rao SV. Darbarwar M. Synthesis 1989, 139 <A NAME="RT06804SS-10B">10b</A> Rao SV. Darbarwar M. Synth. Commun. 1989, 19: 2713 <A NAME="RT06804SS-11A">11a</A> Macias FA. Varela RM. Torres A. Molinillo JMG. Tetrahedron Lett. 1999, 40: 4725 <A NAME="RT06804SS-11B">11b</A> Macias FA. Molinillo JMG. Varela RM. Torres A. Fronzek FR. J. Org. Chem. 1994, 59: 8261 <A NAME="RT06804SS-12A">12a</A> Stefinovic M. Snieckus V. J. Org. Chem. 1998, 63: 2808 <A NAME="RT06804SS-12B">12b</A> Kishuku H. Shindo M. Shishido K. Chem. Commun. 2003, 350 <A NAME="RT06804SS-12C">12c</A> Sabui SK. Venkateswaran RV. Tetrahedron Lett. 2004, 45: 983 <A NAME="RT06804SS-13">13</A> Lutz RE. Codington JF. Rowlett RJ. Deinet AJ. Bailey PS. J. Am. Chem. Soc. 1946, 68: 1810