Synlett, Inhaltsverzeichnis Synlett 2013; 24(7): 851-854DOI: 10.1055/s-0032-1318391 letter © Georg Thieme Verlag Stuttgart · New York A Simple and Efficient Synthesis of Dibenzothiophene via BF3·OEt2-Promoted Intramolecular Annulation Xiaobo Shang a Department of Chemistry, Zhejiang University, Xixi Campus, Hangzhou 310028, P. R. of China Fax: +86(571)88273314 eMail: chenwzz@zju.edu.cn , Wanzhi Chen* a Department of Chemistry, Zhejiang University, Xixi Campus, Hangzhou 310028, P. R. of China Fax: +86(571)88273314 eMail: chenwzz@zju.edu.cn , Yingming Yao* b College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. of China › Institutsangaben Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract A simple and efficient protocol promoted by BF3·OEt2 for synthesizing functionalized dibenzothiophenes (DBTs) has been demonstrated. The annulation condition can tolerate a variety of functional groups. Key words Key wordsdibenzothiophenes - cyclization - Lewis acid - triazene Volltext Referenzen References and Notes 1 Ho TC. Catal. Today 2004; 98: 3 2 Gao J, Li L, Meng Q, Li R, Jiang H, Li H, Hu W. J. Mater. Chem. 2007; 17: 1421 3 Martin-Santamaria S, Rodriguez J.-J, de Pascual-Teresa S, Gordon S, Bengtsson M, Garrido-Laguna I, Rubio-Viqueira B, Lopez-Casas PP, Hidalgo M, de Pascual-Teresa B, Ramos A. Org. Biomol. Chem. 2008; 6: 3486 4a Andrews MD. Sci. Synth. 2000; 10: 211 4b Rayner CM, Graham MA. Sci. Synth. 2000; 10: 155 4c Gilchrist TL, Higgins SJ. Sci. Synth. 2000; 10: 185 4d Gingras M, Raimundo J.-C, Chabre IM. Angew. Chem. Int. Ed. 2006; 45: 1686 5 Gilman H, Jacoby AL. J. Org. Chem. 1938; 3: 108 6 Sanz R, Fernandez Y, Castroviejo MP, Perez A, Fananas FJ. J. Org. Chem. 2006; 71: 6291 7 Kienle M, Unsinn A, Knochel P. Angew. Chem. Int. Ed. 2010; 49: 4751 8 Takashi O, Mayumi F, Daiki S, Keiji M. Adv. Synth. Catal. 2001; 343: 166 9 Samanta R, Antonchick AP. Angew. Chem. Int. Ed. 2011; 50: 5217 10 Jepsen TH, Larsen M, Jorgensen M, Solanko KA, Bond AD, Kadziola A, Nielsen MB. Eur. J. Org. Chem. 2011; 1: 53 11 Korang J, Grither WR, McCulla RD. J. Am. Chem. Soc. 2010; 132: 4466 12 Nayak PK, Agarwal N, Periasamy N. J. Chem. Sci. 2010; 122: 119 13 Kimball DB, Haley MM. Angew. Chem. Int. Ed. 2002; 41: 3338 14 Liu C, Knochel P. J. Org. Chem. 2007; 72: 7106 15a Yang W, Zhou J, Wang B, Ren H. Chem. Eur. J. 2011; 17: 13665 15b Zhao G, Wang B, Yang W, Ren H. Eur. J. Org. Chem. 2012; 31: 6236 16 Zhou J, Yang W, Wang B, Ren H. Angew. Chem. Int. Ed. 2012; 51: 12293 17a Haraguchi H, Ishikawa H, Mizutani K, Tamura Y, Kinoshita T. Bioorg. Med. Chem. 1998; 6: 339 17b Vogel S, Heilmann J. J. Nat. Prod. 2008; 71: 1237 17c Edwards ML, Stemerick DM, Sunkara PS. J. Med. Chem. 1990; 33: 1948 17d Ducki S, Rennison D, Woo M, Kendall A, Chabert JF. D, Mcgown AT, Lawrence NJ. Bioorg. Med. Chem. 2009; 17: 7698 18a Beadle JR, Korzeniowski SH, Rosenberg DE, Garcia-Slanga BJ, Gokel GW. J. Org. Chem. 1984; 49: 1594 18b Patrick TB, Willaredt RP, DeGonia DJ. J. Org. Chem. 1985; 50: 2232 18c Satyamurthy N, Barria JR, Schmidt DG, Kammerer C, Bida GT, Phelps ME. J. Org. Chem. 1990; 55: 4560 18d Saeki T, Son E.C, Tamao K. Bull. Chem. Soc. Jpn. 2005; 78: 1654 19 Pandya VB, Jain MR, Chaugule BV, Patel JS, Parmar BM, Joshi JK, Patel PR. Synth. Commun. 2012; 42: 497 20 Representative Procedure for the Synthesis of 3a: BF3·OEt2 (2.0 equiv) was added dropwise to the stirred solution of 2a (1 mmol) in anhyd MeCN at 45 °C. The mixture was stirred for 4 h. After the completion of the reaction detected by TLC, it was washed with sat. aq NaHCO3 and extracted with EtOAc. The combined organic extracts were dried over anhyd Na2SO4 and removed under reduced pressure. The product was purified by column chromatography to give 3a as a white solid (80% yield); mp 68–71 °C. 1H NMR (400 MHz, CDCl3): δ = 8.84 (s, 1 H), 8.22–8.26 (m, 1 H), 8.11–8.14 (m, 1 H), 7.84–7.90 (m, 2 H), 7.48–7.51 (m, 2 H), 4.46 (q, J = 6.8 Hz, 2 H), 1.47 (t, J = 7.2 Hz, 3 H). 13C NMR (100 MHz, CDCl3): δ = 166.7, 144.2, 139.6, 135.5, 135.2, 127.3, 126.8, 124.8, 123.1, 122.8, 122.5, 121.9, 61.1, 14.4. IR (thin film): 3065, 2924, 1710, 1267, 1100, 1025 cm–1. MS (EI): m/z (%) = 256 (97) [M+], 241 (14), 228 (39), 211 (100), 183 (58), 139 (54). HRMS (EI–TOF): m/z [M+] calcd for C15H12O2S: 256.0558; found: 256.0566. Zusatzmaterial Zusatzmaterial Supporting Information
