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Synlett 2017; 28(10): 1201-1208
DOI: 10.1055/s-0036-1558959
letter
© Georg Thieme Verlag Stuttgart · New York

Ligand-Controlled Chemoselective One-Pot Synthesis of Dibenzothiazepinones and Dibenzoxazepinones via Twice Copper-Catalyzed Cross-Coupling

Yanyu Chen
a   School of Perfume and Aroma Technology, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai 201418, P. R. of China
,
Qiujun Peng
a   School of Perfume and Aroma Technology, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai 201418, P. R. of China
,
Rong Zhang
a   School of Perfume and Aroma Technology, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai 201418, P. R. of China
,
Jian Hu
a   School of Perfume and Aroma Technology, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai 201418, P. R. of China
,
Yijun Zhou
b   Shanghai Research Institute of Fragrance and Flavor Industry, 480 Nanning Road, Shanghai 200232, P. R. of China   Email: xulanting@sit.edu.cn
,
Lanting Xu*
b   Shanghai Research Institute of Fragrance and Flavor Industry, 480 Nanning Road, Shanghai 200232, P. R. of China   Email: xulanting@sit.edu.cn
,
Xianhua Pan*
b   Shanghai Research Institute of Fragrance and Flavor Industry, 480 Nanning Road, Shanghai 200232, P. R. of China   Email: xulanting@sit.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 23 December 2016

Accepted after revision: 04 February 2017

Publication Date:
27 February 2017 (online)

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Abstract

A highly efficient and generally applicable protocol, starting from 2-bromobenzamides and 2-bromo(thio)phenols via twice copper-catalyzed couplings to afford dibenzothiazepines and dibenzoxazepinones has been developed. High levels of yield and chemoselectivity are achieved in a single-pot reaction by using an appropriate ligand. Moreover, this facile methodology allows rapid access to a variety of bio­active compounds and known psychotropic drug, which should broaden its application in organic synthesis.

Key words

copper-Catalyzed - dibenzothiazepinone - dibenzoxazepinone - chemoselectivity - ligands - one-pot

Supporting Information

Primary Data

    Primary data for this article are available online at https://zenodo.org/record/4610225 and can be cited using the following DOI: 10.5281/zenodo.4610225. Please note that the DOI for the Primary Data associated with this article was updated on April 20, 2021.

  • Primary Data
 

  • References

    • 1a Pauwels R, Andries K, Desmyter J, Schols D, Kukla MJ, Breslin HJ, Raeymaeckers A, Van Gelder J, Woestenborghs R, Heykants J. Nature (London, U.K.) 1990; 343: 470-470
    • 1b Hargrave KD, Proudfoot JR, Grozinger KG, Cullen E, Kapadia SR, Patel UR, Fuchs VU, Mauldin SC, Vitous J. J. Med. Chem. 1991; 34: 2231-2231
    • 1c Inoue H, Konda M, Hashiyama T, Otsuka H, Takahashi K, Gaino M, Date T, Aoe K, Takeda M. J. Med. Chem. 1991; 34: 675-675
    • 1d Das J, Floyd DM, Kimball SD, Duff KJ, Lago MW, Krapcho J, White RE, Ridgewell RE, Obermeier MT. J. Med. Chem. 1992; 35: 2610-2610
    • 1e Goldstein JM, Arvanitis LA. CNS Drug Rev. 1995; 1: 50-50
    • 1f Murakami Y, Hara H, Okada T, Hashizume H, Kii M, Ishihara Y, Ishikawa M, Shimamura M, Mihara S, Kato G, Hanasaki K, Hagishita S, Fujimoto M. J. Med. Chem. 1999; 42: 2621-2621
    • 1g Levy O, Erez M, Varon D, Keinan E. Bioorg. Med. Chem. Lett. 2001; 11: 2921-2921
    • 1h Storck P, Aubertin AM, Grierson DS. Tetrahedron Lett. 2005; 46: 2919-2919
    • 1i Vilar S, Santana L, Uriarte E. J. Med. Chem. 2006; 49: 1118-1118
    • 1j Al-Tel TH, Al-Qawasmeh RA, Schmidt MF, Al-Aboudi A, Rao SN, Sabri SS, Voelter W. J. Med. Chem. 2009; 52: 6484-6484
    • 2a Burstein ES, Gardell LR. WO 2008118141, 2008
    • 2b Pettersson H, Bülow A, Ek F, Jensen J, Ottesen LK, Fejzic A, Ma JN, Del Tredici AL, Currier EA, Gardell LR. J. Med. Chem. 2009; 52: 1975-1975
  • 3 Binaschi M, Boldetti A, Gianni M, Maggi CA, Gensini M, Bigioni M, Parlani M, Giolitti A, Fratelli M, Valli C, Terao M, Garattini E. ACS Med. Chem. Lett. 2010; 1: 411-411
  • 4 Newton GL, Buchmeier N, La Clair JJ, Fahey RC. Bioorg. Med. Chem. 2011; 19: 3956-3956
    • 5a Merluzzi VJ, Hargrave KD, Labadia M, Grozinger K, Skoog M, Wu JC, Shih CK, Eckner K, Hattox S, Adams J. Science 1990; 250: 1411-1411
    • 5b Klunder JM, Hargrave KD, West M, Cullen E, Pal K, Behnke ML, Kapadia SR, McNeil DW, Wu JC, Chow GC. J. Med. Chem. 1992; 35: 1887-1887
    • 5c Li R, Farmer P, Wang J, Boyd R, Cameron T, Quilliam M, Walter J, Howlett S. Drug Des. Discovery 1995; 12: 337-337
    • 6a Kumar KV, Kanhaiya L, Suhail A, David L. WO 2006113425, 2006
    • 6b Thase ME, Macfadden W, Weisler RH, Chang W, Paulsson B, Khan A, Calabrese JR. J. Clin. Psychopharmacol. 2006; 26: 600-600
    • 7a David J, Grewal R. Indian J. Exp. Biol. 1974; 12: 225-225
    • 7b Nagarajan K. Indian J. Chem. 1974; 12: 270-270
    • 7c Nagarajan K, David J, Kulkarni Y, Hendi S, Shenoy S, Upadhyaya P. Eur. J. Med. Chem. 1986; 21: 21-21
    • 8a Jann MW. Pharmacotherapy 1991; 11: 179-179
    • 8b Liao Y, Venhuis BJ, Rodenhuis N, Timmerman W, Wikström H. J. Med. Chem. 1999; 42: 2235-2235
    • 9a Allen RC, Reitano PA, Urbach H. J. Med. Chem. 1978; 21: 838-838
    • 9b Konstantinova A, Gerasimova T, Kozlova M, Petrenko N. Chem. Heterocycl. Compd. 1989; 25: 451-451
    • 9c Samet AV, Marshalkin VN, Kislyi KA, Chernysheva NB, Strelenko YA, Semenov VV. J. Org. Chem. 2005; 70: 9371-9371
    • 9d Samet A, Kislyi K, Marshalkin V, Semenov V. Russ. Chem. Bull. 2006; 55: 549-549
    • 10a Lu SM, Alper H. J. Am. Chem. Soc. 2005; 127: 14776-14776
    • 10b Yang Q, Cao H, Robertson A, Alper H. J. Org. Chem. 2010; 75: 6297-6297
  • 11 Tsvelikhovsky D, Buchwald SL. J. Am. Chem. Soc. 2011; 133: 14228-14228
    • 12a Yang B, Tan X, Guo R, Chen S, Zhang Z, Chu X, Xie C, Zhang D, Ma C. J. Org. Chem. 2014; 79: 8040-8040
    • 12b Zhou Y, Zhu J, Li B, Zhang Y, Feng J, Hall A, Shi J, Zhu W. Org. Lett. 2016; 18: 380-380
    • 12c Yang X, Shan G, Rao Y. Org. Lett. 2013; 15: 2334-2334
    • 12d Zhao Y, Dai Q, Chen Z, Zhang Q, Bai Y, Ma C. Acs Comb. Sci. 2013; 15: 130-130
    • 12e Shen C, Neumann H, Wu XF. Green Chem. 2015; 17: 2994-2994
    • 12f Zhang Z, Dai Z, Ma X, Liu Y, Ma X, Li W, Ma C. Org. Chem. Front. 2016; 3: 799-799
    • 13a Zou B, Yuan Q, Ma D. Angew. Chem. Int. Ed. 2007; 46: 2598-2598
    • 13b Zou B, Yuan Q, Ma D. Org. Lett. 2007; 9: 4291-4291
    • 13c Wang B, Lu B, Jiang Y, Zhang Y, Ma D. Org. Lett. 2008; 10: 2761-2761
    • 13d Ma D, Xie S, Xue P, Zhang X, Dong J, Jiang Y. Angew. Chem. 2009; 121: 4286-4286
    • 13e Ma D, Geng Q, Zhang H, Jiang Y. Angew. Chem. 2010; 122: 1313-1313
    • 13f Ma D, Lu X, Shi L, Zhang H, Jiang Y, Liu X. Angew. Chem. Int. Ed. 2011; 50: 1118-1118
    • 13g Xu L, Jiang Y, Ma D. Org. Lett. 2012; 14: 1150-1150
    • 13h Xu L, Peng Y, Pan Q, Jiang Y, Ma D. J. Org. Chem. 2013; 78: 3400-3400
    • 13i Martín R, Rodríguez Rivero M, Buchwald SL. Angew. Chem. Int. Ed. 2006; 45: 7079-7079
    • 13j Bao W, Liu Y, Lv X, Qian W. Org. Lett. 2008; 10: 3899-3899
    • 13k Coste A, Toumi M, Wright K, Razafimahaléo V, Couty F, Marrot J, Evano G. Org. Lett. 2008; 10: 3841-3841
    • 13l Liu X, Fu H, Jiang Y, Zhao Y. Angew. Chem. 2009; 121: 354-354
    • 14a Evano G, Blanchard N, Toumi M. Chem. Rev. 2008; 108: 3054-3054
    • 14b Ma D, Cai Q. Acc. Chem. Res. 2008; 41: 1450-1450
    • 14c Monnier F, Taillefer M. Angew. Chem. Int. Ed. 2009; 48: 6954-6954
    • 14d Sperotto E, Van Klink GP. M, Van Koten G, De Vries JG. Dalton Trans. 2010; 39: 10338-10338
    • 14e Surry DS, Buchwald SL. Chem. Sci. 2010; 1: 13-13
    • 15a Cai Q, Zou B, Ma D. Angew. Chem. Int. Ed. 2006; 45: 1276-1276
    • 15b Xie X, Chen Y, Ma D. J. Am. Chem. Soc. 2006; 128: 16050-16050
    • 15c Cai Q, Zhang H, Zou B, Xie X, Zhu W, He G, Wang J, Pan X, Chen Y, Yuan Q, Jiang Y, Ma D. Pure Appl. Chem. 2009; 81: 227-227
    • 16a Jiang Y, Xu L, Zhou C, Ma D. Cu-Catalyzed Ullmann-Type C-Heteroatom Bond Formation: The Key Role of Dinucleating Ancillary Ligands. In RSC Catalysis Series. RCS; Cambridge: 2013: 1
      Google Scholar
    • 16b Maiti D, Buchwald SL. J. Am. Chem. Soc. 2009; 131: 17423-17423
  • 17 Kitching MO, Hurst TE, Snieckus PV. Angew. Chem. Int. Ed. 2012; 124: 2979-2979