Synthesis, Inhaltsverzeichnis PAPER© Georg Thieme Verlag Stuttgart ˙ New YorkFunctionalization of the Benzo[c][1,2,5]thiadiazole Scaffold via Mg-, Zn- and Mn-IntermediatesSilvia Zimdars, Heinz Langhals, Paul Knochel*Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, 81377 München, GermanyFax: +49(89)218077680; e-Mail: paul.knochel@cup.uni-muenchen.de; Artikel empfehlen Abstract Artikel einzeln kaufen(opens in new window) Alle Artikel dieser Rubrik(opens in new window) Abstract The metalation of all positions of the benzo[c][1,2,5]thiadiazole scaffold using LiCl-solubilized TMP-bases is demonstrated on various substrates. Thus, unsymmetrically substituted benzothiadiazole derivatives and a new fused thiadiazoloindazole have been prepared. Key words organometallic reagents - metalation - bicyclic compounds - heterocycles - benzo[c][1,2,5]thiadiazole Volltext Referenzen References <A NAME="RT15911SS-1A">1a</A> Kunz T. Knochel P. Chem. Eur. J. 2011, 17: 866 <A NAME="RT15911SS-1B">1b</A> Kienle M. Unsinn A. Knochel P. Angew. Chem. Int. Ed. 2010, 49: 4751 <A NAME="RT15911SS-1C">1c</A> Metzger A. Melzig L. Knochel P. Synthesis 2010, 2853 <A NAME="RT15911SS-1D">1d</A> Despotopoulou C. Gignoux C. McConnell D. Knochel P. Synthesis 2009, 3661 <A NAME="RT15911SS-2A">2a</A> Lovell BV. Marmura MJ. Curr. Opin. Neurol. 2010, 23: 254 <A NAME="RT15911SS-2B">2b</A> Kamen L. Henney HR. Runyan JD. Curr. Med. Res. Opin 2008, 24: 425 <A NAME="RT15911SS-3A">3a</A> Zheng Q. Chen S. Zhang B. Wang L. Tang C. Katz HE. Org. Lett. 2011, 13: 324 <A NAME="RT15911SS-3B">3b</A> Xu E. Zhong H. Lai H. Zeng D. Zhang J. Zhu W. Fang Q. Macromol. Chem. Phys. 2010, 211: 651 <A NAME="RT15911SS-3C">3c</A> Clarke T. Ballantyne A. Jamieson F. Brabec C. Nelson J. Durrante J. Chem. Commun. 2009, 89 <A NAME="RT15911SS-4">4</A> Sonar P. Soh MS. Cheng YH. Henssler JT. Sellinger A. Org. Lett. 2010, 12: 3292 <A NAME="RT15911SS-5">5</A> Pu K.-Y. Li K. Liu B. Adv. Funct. Mater. 2010, 20: 2770 <A NAME="RT15911SS-6A">6a</A> Du J. Xu E. Zhong H. Yu F. Liu C. Wu H. Zeng D. Ren S. Sun J. Liu Y. Cao A. Fang Q. J. Polym. Sci., Part A: Polym. Chem. 2008, 46: 1376 <A NAME="RT15911SS-6B">6b</A> Ju JU. Jung SO. Zhao QH. Kim YH. Je JT. Kwon SK. Bull. Korean Chem. Soc. 2008, 29: 335 <A NAME="RT15911SS-6C">6c</A> Lash TD. Wijesinghe C. Osuma AT. Patel JR. Tetrahedron Lett. 1997, 38: 2031 <A NAME="RT15911SS-6D">6d</A> Takagi K. Tomoeda M. Chem. Pharm. Bull. 1980, 28: 1909 <A NAME="RT15911SS-6E">6e</A> Komin AP. Carmack M. J. Heterocycl. Chem. 1975, 12: 829 <A NAME="RT15911SS-7">7</A> Pilgram K. Skiles RD. J. Heterocycl. Chem. 1970, 7: 629 <A NAME="RT15911SS-8A">8a</A> Zoombelt AP. Fonrodona M. Wienk MM. Sieval AB. Hummelen JC. Janssen RAJ. Org. Lett. 2009, 11: 903 <A NAME="RT15911SS-8B">8b</A> Melucci M. Favaretto L. Bettini C. Gazzano M. Camaioni N. Maccagnani P. Ostoja P. Monari M. Barbarella G. Chem. Eur. J. 2007, 13: 10046 <A NAME="RT15911SS-8C">8c</A> Zhang M. Tsao HN. Pisula W. Yang C. Mishra AK. Müllen K. J. Am. Chem. Soc. 2007, 129: 3472 <A NAME="RT15911SS-8D">8d</A> Yao Y.-H. Kung L.-R. Hsu C.-S. J. Polym. Res. 2006, 13: 277 <A NAME="RT15911SS-8E">8e</A> van Mullekom HAM. Vekemans JAJM. Meijer EW. Chem. Eur. J. 1998, 4: 1235 <A NAME="RT15911SS-9A">9a</A> Bijleveld JC. Shahid M. Gilot J. Wienk MM. Janssen RAJ. Adv. Funct. Mater. 2009, 19: 3262 <A NAME="RT15911SS-9B">9b</A> Sonar P. Singh SP. Leclère P. Surin M. Lazzaroni R. Lin TT. Dodabalapur A. Sellinger A. J. Mater. Chem. 2009, 19: 3228 <A NAME="RT15911SS-9C">9c</A> Wunderlich SH. Kienle M. Knochel P. Angew. Chem. Int. Ed. 2009, 48: 7256 <A NAME="RT15911SS-9D">9d</A> Jørgensen M. Krebs FC. J. Org. Chem. 2005, 70: 6004 <A NAME="RT15911SS-9E">9e</A> Komin AP. Carmack M. J. Heterocycl. Chem. 1975, 12: 829 <A NAME="RT15911SS-9F">9f</A> Pilgram K. Zupan M. J. Org. Chem. 1971, 36: 207 <A NAME="RT15911SS-10A">10a</A> DaSilveira Neto BA. Lopes ASA. Ebeling G. Gonçalves RS. Costa VEU. Quina FH. Dupont J. Tetrahedron 2005, 61: 10975 <A NAME="RT15911SS-10B">10b</A> Michaelis A. Storbeck O. Justus Liebgis Ann. Chem. 1893, 274: 263 <A NAME="RT15911SS-10C">10c</A> Michaelis A. Erdmann G. Ber. Dtsch. Chem. Ges. 1895, 28: 2192 <A NAME="RT15911SS-11A">11a</A> Clososki G. Rohbogner C. Knochel P. Angew. Chem. Int. Ed. 2007, 46: 7681 <A NAME="RT15911SS-11B">11b</A> Rohbogner C. Wagner A. Clososki G. Knochel P. Org. Synth. 2009, 86: 374 <A NAME="RT15911SS-12A">12a</A> Negishi E. Acc. Chem. Res. 1982, 15: 340 <A NAME="RT15911SS-12B">12b</A> Negishi E. Valente LF. Kobayashi M. J. Am. Chem. Soc. 1980, 102: 3298 <A NAME="RT15911SS-12C">12c</A> Negishi E. King AO. Okukado N. J. Org. Chem. 1977, 42: 1821 <A NAME="RT15911SS-13">13</A> Vagin S. Frickenschmidt A. Kammerer B. Hanack M. Eur. J. Org. Chem. 2005, 3271 <A NAME="RT15911SS-14A">14a</A> Krasovskiy A. Krasovskaya V. Knochel P. Angew. Chem. Int. Ed. 2006, 45: 2958 <A NAME="RT15911SS-14B">14b</A> Lin W. Baron O. Knochel P. Org. Lett. 2006, 8: 5673 <A NAME="RT15911SS-15">15</A> Hosomi A. Shirahata A. Araki Y. Sakurai H. J. Org. Chem. 1981, 46: 4631 <A NAME="RT15911SS-16">16</A> Piller F. Appukkuttan P. Gavryushin A. Helm M. Knochel P. Angew. Chem. Int. Ed. 2008, 47: 6802 <A NAME="RT15911SS-17A">17a</A> Knochel P. Yeh MCP. Berk SC. Talbert J. J. Org. Chem. 1988, 53: 2390 <A NAME="RT15911SS-17B">17b</A> Dübner F. Knochel P. Angew. Chem. Int. Ed. 1999, 38: 379