Synthesis, Inhaltsverzeichnis PAPER © Georg Thieme Verlag Stuttgart · New York Regioselective Synthesis of Oxepin- and Oxocin-Annulated 2-Quinolones Shital 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 1a Abd E. Hisham A. Pharmazie 1997, 52: 28 1b Sun HB. Qing FL. Chen XF. Synthesis 1997, 1249 1c Nevile CF. Grundon MF. Ramchandran VN. Reisch G. Reisch J. J. Chem. Soc., Perkin Trans. 1 1991, 2261 2a Staubitz A. Dohle W. Knochel P. Synthesis 2003, 233 2b Lee YR. Kweon HI. Koh WS. Min KR. Kim Y. Lee SH. Synthesis 2001, 1851 2c Ullrich T. Girard F. Tetrahedron Lett. 2003, 44: 4207 3a Yang Z.-Y. Xia Y. Xia P. Brossi A. Lee K.-H. Tetrahedron Lett. 1999, 40: 4505 3b Ye J.-H. Ling K.-Q. Zhang Y. Li N. Xu J.-H. J. Chem. Soc., Perkin Trans. 1 1999, 2017 3c Majumdar KC. Ghosh SK. Biswas P. Monatsh. Chem. 2000, 31: 967 4 Yet L. Chem. Rev. 2000, 100: 2963 For recent reviews, see: 5a Trnka TM. Grubbs RH. Acc. Chem. Res. 2001, 34: 18 5b Fürstner A. Angew. Chem. Int. Ed. 2000, 39: 3012 5c Blechert S. Connon S. Angew. Chem. Int. Ed. 2003, 42: 1900 5d Poulsen CS. Madsen R. Synthesis 2003, 1 For some recent applications of RCM reaction in medium ring oxacycle formation, see: 6a Mamouni R. Soukri M. Lazar S. Akssira M. Guillaumet G. Tetrahedron Lett. 2004, 45: 2631 6b Van Otterlo WAL. Pathak R. de Koning CB. Synlett 2003, 1859 6c Pain C. Celanire S. Guillaumet G. Joseph B. Synlett 2003, 2089 7a Chattopadhyay SK. Maity S. Panja S. Tetrahedron Lett. 2002, 43: 7781 7b Chattopadhyay SK. Paul BK. Maity S. Chem. Lett. 2003, 32: 1190 For some recent reviews on Claisen rearrangement, see: 8a Nubbemeyer U. Synthesis 2003, 961 8b Castro AMM. Chem. Rev. 2004, 104: 2939 8c Blechert S. Synthesis 1989, 71 9 Chamberlin TR. Grundon MF. Tetrahedron Lett. 1967, 3547 10a Rao SV. Darbarwar M. Synthesis 1989, 139 10b Rao SV. Darbarwar M. Synth. Commun. 1989, 19: 2713 11a Macias FA. Varela RM. Torres A. Molinillo JMG. Tetrahedron Lett. 1999, 40: 4725 11b Macias FA. Molinillo JMG. Varela RM. Torres A. Fronzek FR. J. Org. Chem. 1994, 59: 8261 12a Stefinovic M. Snieckus V. J. Org. Chem. 1998, 63: 2808 12b Kishuku H. Shindo M. Shishido K. Chem. Commun. 2003, 350 12c Sabui SK. Venkateswaran RV. Tetrahedron Lett. 2004, 45: 983 13 Lutz RE. Codington JF. Rowlett RJ. Deinet AJ. Bailey PS. J. Am. Chem. Soc. 1946, 68: 1810