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DOI: 10.1055/s-0036-1558959
Ligand-Controlled Chemoselective One-Pot Synthesis of Dibenzothiazepinones and Dibenzoxazepinones via Twice Copper-Catalyzed Cross-Coupling
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-potSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1558959.
- Supporting Information
- CIF File
Primary Data
- 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.
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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
-
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