Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart ˙ New York Functionalization of the Benzo[c][1,2,5]thiadiazole Scaffold via Mg-, Zn- and Mn-Intermediates Silvia 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; Recommend Article Abstract Buy Article All articles of this category 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 Full Text References References 1a Kunz T. Knochel P. Chem. Eur. J. 2011, 17: 866 1b Kienle M. Unsinn A. Knochel P. Angew. Chem. Int. Ed. 2010, 49: 4751 1c Metzger A. Melzig L. Knochel P. Synthesis 2010, 2853 1d Despotopoulou C. Gignoux C. McConnell D. Knochel P. Synthesis 2009, 3661 2a Lovell BV. Marmura MJ. Curr. Opin. Neurol. 2010, 23: 254 2b Kamen L. Henney HR. Runyan JD. Curr. Med. Res. Opin 2008, 24: 425 3a Zheng Q. Chen S. Zhang B. Wang L. Tang C. Katz HE. Org. Lett. 2011, 13: 324 3b Xu E. Zhong H. Lai H. Zeng D. Zhang J. Zhu W. Fang Q. Macromol. Chem. Phys. 2010, 211: 651 3c Clarke T. Ballantyne A. Jamieson F. Brabec C. Nelson J. Durrante J. Chem. Commun. 2009, 89 4 Sonar P. Soh MS. Cheng YH. Henssler JT. Sellinger A. Org. Lett. 2010, 12: 3292 5 Pu K.-Y. Li K. Liu B. Adv. Funct. Mater. 2010, 20: 2770 6a 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 6b Ju JU. Jung SO. Zhao QH. Kim YH. Je JT. Kwon SK. Bull. Korean Chem. Soc. 2008, 29: 335 6c Lash TD. Wijesinghe C. Osuma AT. Patel JR. Tetrahedron Lett. 1997, 38: 2031 6d Takagi K. Tomoeda M. Chem. Pharm. Bull. 1980, 28: 1909 6e Komin AP. Carmack M. J. Heterocycl. Chem. 1975, 12: 829 7 Pilgram K. Skiles RD. J. Heterocycl. Chem. 1970, 7: 629 8a Zoombelt AP. Fonrodona M. Wienk MM. Sieval AB. Hummelen JC. Janssen RAJ. Org. Lett. 2009, 11: 903 8b Melucci M. Favaretto L. Bettini C. Gazzano M. Camaioni N. Maccagnani P. Ostoja P. Monari M. Barbarella G. Chem. Eur. J. 2007, 13: 10046 8c Zhang M. Tsao HN. Pisula W. Yang C. Mishra AK. Müllen K. J. Am. Chem. Soc. 2007, 129: 3472 8d Yao Y.-H. Kung L.-R. Hsu C.-S. J. Polym. Res. 2006, 13: 277 8e van Mullekom HAM. Vekemans JAJM. Meijer EW. Chem. Eur. J. 1998, 4: 1235 9a Bijleveld JC. Shahid M. Gilot J. Wienk MM. Janssen RAJ. Adv. Funct. Mater. 2009, 19: 3262 9b Sonar P. Singh SP. Leclère P. Surin M. Lazzaroni R. Lin TT. Dodabalapur A. Sellinger A. J. Mater. Chem. 2009, 19: 3228 9c Wunderlich SH. Kienle M. Knochel P. Angew. Chem. Int. Ed. 2009, 48: 7256 9d Jørgensen M. Krebs FC. J. Org. Chem. 2005, 70: 6004 9e Komin AP. Carmack M. J. Heterocycl. Chem. 1975, 12: 829 9f Pilgram K. Zupan M. J. Org. Chem. 1971, 36: 207 10a DaSilveira Neto BA. Lopes ASA. Ebeling G. Gonçalves RS. Costa VEU. Quina FH. Dupont J. Tetrahedron 2005, 61: 10975 10b Michaelis A. Storbeck O. Justus Liebgis Ann. Chem. 1893, 274: 263 10c Michaelis A. Erdmann G. Ber. Dtsch. Chem. Ges. 1895, 28: 2192 11a Clososki G. Rohbogner C. Knochel P. Angew. Chem. Int. Ed. 2007, 46: 7681 11b Rohbogner C. Wagner A. Clososki G. Knochel P. Org. Synth. 2009, 86: 374 12a Negishi E. Acc. Chem. Res. 1982, 15: 340 12b Negishi E. Valente LF. Kobayashi M. J. Am. Chem. Soc. 1980, 102: 3298 12c Negishi E. King AO. Okukado N. J. Org. Chem. 1977, 42: 1821 13 Vagin S. Frickenschmidt A. Kammerer B. Hanack M. Eur. J. Org. Chem. 2005, 3271 14a Krasovskiy A. Krasovskaya V. Knochel P. Angew. Chem. Int. Ed. 2006, 45: 2958 14b Lin W. Baron O. Knochel P. Org. Lett. 2006, 8: 5673 15 Hosomi A. Shirahata A. Araki Y. Sakurai H. J. Org. Chem. 1981, 46: 4631 16 Piller F. Appukkuttan P. Gavryushin A. Helm M. Knochel P. Angew. Chem. Int. Ed. 2008, 47: 6802 17a Knochel P. Yeh MCP. Berk SC. Talbert J. J. Org. Chem. 1988, 53: 2390 17b Dübner F. Knochel P. Angew. Chem. Int. Ed. 1999, 38: 379