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Angewandte Chemie - International Edition

Volumn 51, Issue 12, 2012, Pages 2925-2929

Copper-catalyzed cross-coupling interrupted by an opportunistic smiles rearrangement: An efficient domino approach to dibenzoxazepinones

(3) Kitching, Matthew O a Hurst, Timothy E a Snieckus, Victor a

a QUEEN S UNIVERSITY (Canada)

Author keywords

C N bond formation; C O bond formation; copper; domino reactions; Smiles rearrangement

Indexed keywords

BENZAMIDES; BOND FORMATION; C-O BOND FORMATION; CROSS-COUPLINGS; DOMINO REACTIONS; MECHANISTIC DATA; REGIOSELECTIVE SYNTHESIS; SMILES REARRANGEMENT;

AMIDES; PHENOLS; REACTION KINETICS;

COPPER;

EID: 84858162567 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201106786 Document Type: Article

Times cited : (63)

References (49)

1
- 58349102704
- For palladium amination, see: a)D. S. Surry, S. L. Buchwald, Angew. Chem. 2008, 120, 6438-6461
- (2008) Angew. Chem. , vol.120 , pp. 6438-6461
- Surry, D.S.¹ Buchwald, S.L.²

2
- 52049105452
- for copper, see
- Angew. Chem. Int. Ed. 2008, 47, 6338-6361; for copper, see
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 6338-6361

3
- 0346749657
- K. Kunz, U. Scholz, D. Ganzer, Synlett 2003, 2428-2439
- (2003) Synlett , pp. 2428-2439
- Kunz, K.¹ Scholz, U.² Ganzer, D.³

4
- 4143116053
- S. V. Ley, A. W. Thomas, Angew. Chem. 2003, 115, 5558-5607
- (2003) Angew. Chem. , vol.115 , pp. 5558-5607
- Ley, S.V.¹ Thomas, A.W.²

5
- 0345708168
- Angew. Chem. Int. Ed. 2003, 42, 5400-5449.
- (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 5400-5449

6
- 0001237986
- L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170
- (1993) Angew. Chem. , vol.105 , pp. 137-170
- Tietze, L.F.¹ Beifuss, U.²

7
- 33750173220
- Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163.
- (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 131-163

8
- 78449260529
- As a selected example, see.
- As a selected example, see:, B. P. Fors, S. L. Buchwald, J. Am. Chem. Soc. 2010, 132, 15914-15917.
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 15914-15917
- Fors, B.P.¹ Buchwald, S.L.²

9
- 84858210448
- As a selected example, see
- As a selected example, see:, J. Panteleev, L. Zhang, M. Lautens, Angew. Chem. 2011, 123, 9255-9258
- (2011) Angew. Chem. , vol.123 , pp. 9255-9258
- Panteleev, J.¹ Zhang, L.² Lautens, M.³

10
- 80052834742
- Angew. Chem. Int. Ed. 2011, 50, 9089-9092.
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 9089-9092

11
- 34250627489
- M. D'Souza, T. J. J. Müller, Chem. Soc. Rev. 2007, 36, 1095-1108.
- (2007) Chem. Soc. Rev. , vol.36 , pp. 1095-1108
- D'Souza, M.¹ Müller, T.J.J.²

12
- 70350607555
- F. Monnier, M. Taillefer, Angew. Chem. 2009, 121, 7088-7105
- (2009) Angew. Chem. , vol.121 , pp. 7088-7105
- Monnier, F.¹ Taillefer, M.²

13
- 70349786460
- Angew. Chem. Int. Ed. 2009, 48, 6954-6971.
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 6954-6971

14
- 0033617396
- A. V. Kalinin, J. F. Bower, P. Riebel, V. Snieckus, J. Org. Chem. 1999, 64, 2986-2987.
- (1999) J. Org. Chem. , vol.64 , pp. 2986-2987
- Kalinin, A.V.¹ Bower, J.F.² Riebel, P.³ Snieckus, V.⁴

15
- 79957833098
- E. Racine, F. Monnier, J.-P. Vors, M. Taillefer, Org. Lett. 2011, 13, 2818-2821.
- (2011) Org. Lett. , vol.13 , pp. 2818-2821
- Racine, E.¹ Monnier, F.² Vors, J.-P.³ Taillefer, M.⁴

16
- 72249084125
- For example, see: a)D. Maiti, S. L. Buchwald, J. Am. Chem. Soc. 2009, 131, 17423-17429
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 17423-17429
- Maiti, D.¹ Buchwald, S.L.²

17
- 33947644070
- A. Shafir, P. A. Lichtor, S. L. Buchwald, J. Am. Chem. Soc. 2007, 129, 3490-3491
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 3490-3491
- Shafir, A.¹ Lichtor, P.A.² Buchwald, S.L.³

18
- 0037126221
- G. E. Job, S. L. Buchwald, Org. Lett. 2002, 4, 3703-3706
- (2002) Org. Lett. , vol.4 , pp. 3703-3706
- Job, G.E.¹ Buchwald, S.L.²

19
- 49549087576
- F. Monnier, M. Taillefer, Angew. Chem. 2008, 120, 3140-3143
- (2008) Angew. Chem. , vol.120 , pp. 3140-3143
- Monnier, F.¹ Taillefer, M.²

20
- 47749142816
- Angew. Chem. Int. Ed. 2008, 47, 3096-3099.
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 3096-3099

21
- 0020375151
- By intramolecular Friedel-Crafts acylation, see: a)Y. Nagai, A. Irie, H. Nakamura, K. Hino, H. Uno, H. Nishimura, J. Med. Chem. 1982, 25, 1065-1070
- (1982) J. Med. Chem. , vol.25 , pp. 1065-1070
- Nagai, Y.¹ Irie, A.² Nakamura, H.³ Hino, K.⁴ Uno, H.⁵ Nishimura, H.⁶

22
- 34547657325
- by oxidation of dibenzo(b,f)(1,4)-oxazepines, see
- B. S. Wagh, B. P. Patil, M. S. Jam, S. S. Harak, S. B. Wagh, Heterocycl. Commun. 2007, 13, 165-172; by oxidation of dibenzo(b,f)(1,4)-oxazepines, see
- (2007) Heterocycl. Commun. , vol.13 , pp. 165-172
- Wagh, B.S.¹ Patil, B.P.² Jam, M.S.³ Harak, S.S.⁴ Wagh, S.B.⁵

23
- 37049091917
- by Beckmann rearrangement, see
- K. Brewster, R. A. Chittenden, J. M. Harrison, T. D. Inch, C. Brown, J. Chem. Soc. Perkin Trans. 1 1976, 1291-1296; by Beckmann rearrangement, see
- (1976) J. Chem. Soc. Perkin Trans. 1 , pp. 1291-1296
- Brewster, K.¹ Chittenden, R.A.² Harrison, J.M.³ Inch, T.D.⁴ Brown, C.⁵

24
- 0013618921
- K. Nagarajan, C. L. Kulkarni, A. Venkateswarlu, Indian J. Chem. 1974, 12, 247-251
- (1974) Indian J. Chem. , vol.12 , pp. 247-251
- Nagarajan, K.¹ Kulkarni, C.L.² Venkateswarlu, A.³

25
- 52949112936
- [J. Org. Chem. USSR (Engl. Transl.) 1967, 3, 480-482]; by carbonylative coupling, see
- A. T. Troshchenko, T. P. Lobanova, Zh. Org. Khim. 1967, 3, 501-503 [J. Org. Chem. USSR (Engl. Transl.) 1967, 3, 480-482]; by carbonylative coupling, see
- (1967) Zh. Org. Khim. , vol.3 , pp. 501-503
- Troshchenko, A.T.¹ Lobanova, T.P.²

26
- 77956549655
- by Ugi four-component reactions, see
- Q. Yang, H. Cao, A. Robertson, H. Alper, J. Org. Chem. 2010, 75, 6297-6299; by Ugi four-component reactions, see
- (2010) J. Org. Chem. , vol.75 , pp. 6297-6299
- Yang, Q.¹ Cao, H.² Robertson, A.³ Alper, H.⁴

27
- 67649414308
- NAr and amide formation, see
- NAr and amide formation, see
- (2009) Synlett , pp. 1162-1166
- Wu, J.¹ Jiang, Y.² Dai, W.-M.³

28
- 0037926642
- I. G. Abramov, A. V. Smirnov, L. S. Kalandadze, V. N. Sakharov, V. V. Plakhtinskii, Heterocycles 2003, 60, 1611-1614
- (2003) Heterocycles , vol.60 , pp. 1611-1614
- Abramov, I.G.¹ Smirnov, A.V.² Kalandadze, L.S.³ Sakharov, V.N.⁴ Plakhtinskii, V.V.⁵

29
- 27744519603
- A. V. Samet, V. N. Marshalkin, K. A. Kislyi, N. B. Chernysheva, Y. A. Strelenko, V. V. Semenov, J. Org. Chem. 2005, 70, 9371-9376
- (2005) J. Org. Chem. , vol.70 , pp. 9371-9376
- Samet, A.V.¹ Marshalkin, V.N.² Kislyi, K.A.³ Chernysheva, N.B.⁴ Strelenko, Y.A.⁵ Semenov, V.V.⁶

30
- 33747442402
- R. A. Bunce, J. E. Schammerhorn, J. Heterocycl. Chem. 2006, 43, 1031-1035
- (2006) J. Heterocycl. Chem. , vol.43 , pp. 1031-1035
- Bunce, R.A.¹ Schammerhorn, J.E.²

31
- 77957890633
- for solid phase synthesis, see
- H. J. M. Gijsen, D. Berthelot, M. Zaja, B. Brône, I. Geuens, M. Mercken, J. Med. Chem. 2010, 53, 7011-7020; for solid phase synthesis, see
- (2010) J. Med. Chem. , vol.53 , pp. 7011-7020
- Gijsen, H.J.M.¹ Berthelot, D.² Zaja, M.³ Brône, B.⁴ Geuens, I.⁵ Mercken, M.⁶

32
- 0033525809
- X. Ouyang, N. Tamayo, A. S. Kiselyov, Tetrahedron 1999, 55, 2827-2834
- (1999) Tetrahedron , vol.55 , pp. 2827-2834
- Ouyang, X.¹ Tamayo, N.² Kiselyov, A.S.³

33
- 0141656513
- N. D. Hone, J. I. Salter, J. C. Reader, Tetrahedron Lett. 2003, 44, 8169-8172.
- (2003) Tetrahedron Lett. , vol.44 , pp. 8169-8172
- Hone, N.D.¹ Salter, J.I.² Reader, J.C.³

34
- 0003961355
- Pergamon, Elsevier
- J. Clayden, Organolithiums: Selectivity in Synthesis, Pergamon, Elsevier, 2002, pp. 21-90
- (2002) Organolithiums: Selectivity in Synthesis , pp. 21-90
- Clayden, J.¹

35
- 33744510833
- (Ed.: G. Dyker), WileyVCH, New York
- T. Macklin, V. Snieckus, in Handbook of CH Transformations (Ed.:, G. Dyker,), WileyVCH, New York, 2005, pp. 106-119
- (2005) Handbook of CH Transformations , pp. 106-119
- Macklin, T.¹ Snieckus, V.²

36
- 0042291889
- (Ed.: D. Astruc) WileyVCH, New York, .
- C. G. Hartung, V. Snieckus, in Modern Arene Chemistry (Ed.:, D. Astruc,) WileyVCH, New York, 2002, pp. 330-367.
- (2002) Modern Arene Chemistry , pp. 330-367
- Hartung, C.G.¹ Snieckus, V.²

37
- 32344439358
- For HIV-1 RT inhibition, see:, for CNS agents, see
- For HIV-1 RT inhibition, see:, S. Vilar, L. Santan, E. Uriarte, J. Med. Chem. 2006, 49, 1118-1124; for CNS agents, see
- (2006) J. Med. Chem. , vol.49 , pp. 1118-1124
- Vilar, S.¹ Santan, L.² Uriarte, E.³

38
- 0028280136
- for p38 MAP kinase inhibition see
- J. F. F. Liegeois, F. A. Rogister, J. Bruhwyler, J. Damas, T. P. Nguyen, M. O. Inarejos, E. M. G. Chleide, M. G. A. Mercier, J. E. Delarge, J. Med. Chem. 1994, 37, 519-525; for p38 MAP kinase inhibition see
- (1994) J. Med. Chem. , vol.37 , pp. 519-525
- Liegeois, J.F.F.¹ Rogister, F.A.² Bruhwyler, J.³ Damas, J.⁴ Nguyen, T.P.⁵ Inarejos, M.O.⁶ Chleide, E.M.G.⁷ Mercier, M.G.A.⁸ Delarge, J.E.⁹

39
- 77952108879
- as non-carbohydrate inhibitors of E. coli ribosomal A site, see
- A. Dorn, V. Schattel, S. Laufer, Bioorg. Med. Chem. Lett. 2010, 20, 3074-3077; as non-carbohydrate inhibitors of E. coli ribosomal A site, see
- (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 3074-3077
- Dorn, A.¹ Schattel, V.² Laufer, S.³

40
- 8844264639
- for anti-inflammatory activity, see
- S. P. Maddaford, M. Motamed, K. B. Turner, M. S. K. Choi, J. Ramnauth, S. Rakhit, R. R. Hudgins, D. Fabris, P. E. Johnson, Bioorg. Med. Chem. Lett. 2004, 14, 5987-5990; for anti-inflammatory activity, see
- (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 5987-5990
- Maddaford, S.P.¹ Motamed, M.² Turner, K.B.³ Choi, M.S.K.⁴ Ramnauth, J.⁵ Rakhit, S.⁶ Hudgins, R.R.⁷ Fabris, D.⁸ Johnson, P.E.⁹

41
- 0023092285
- J. K. Chakrabarti, T. A. Hicks, Eur. J. Med. Chem. 1987, 22, 161-163.
- (1987) Eur. J. Med. Chem. , vol.22 , pp. 161-163
- Chakrabarti, J.K.¹ Hicks, T.A.²

42
- 0011744071
- J. F. Bunnett, T. Okamoto, J. Am. Chem. Soc. 1956, 78, 5363-5367.
- (1956) J. Am. Chem. Soc. , vol.78 , pp. 5363-5367
- Bunnett, J.F.¹ Okamoto, T.²

43
- 52949122150
- V. Sapegin, V. N. Sakharov, L. S. Kalandadze, A. V. Smirnov, T. A. Khristolyubova, V. V. Plakhtinskii, A. V. Ivashchenko, Mendeleev Commun. 2008, 18, 281-283
- (2008) Mendeleev Commun. , vol.18 , pp. 281-283
- Sapegin, V.¹ Sakharov, V.N.² Kalandadze, L.S.³ Smirnov, A.V.⁴ Khristolyubova, T.A.⁵ Plakhtinskii, V.V.⁶ Ivashchenko, A.V.⁷

44
- 2942599129
- O. Reinaud, P. Capdevielle, M. Maumy, J. Chem. Soc. Perkin Trans. 1 1991, 2129-2134.
- (1991) J. Chem. Soc. Perkin Trans. 1 , pp. 2129-2134
- Reinaud, O.¹ Capdevielle, P.² Maumy, M.³

45
- 80052694174
- During the preparation of this manuscript a report of the synthesis of dibenzoxazepinones also utilizing a Smiles rearrangement solely on electron deficient substrates appeared; see.
- During the preparation of this manuscript a report of the synthesis of dibenzoxazepinones also utilizing a Smiles rearrangement solely on electron deficient substrates appeared; see:, Y. Liu, C. Chu, A. Huang, C. Zhan, Y. Ma, C. Ma, ACS Comb. Sci. 2011, 13, 547-553.
- (2011) ACS Comb. Sci. , vol.13 , pp. 547-553
- Liu, Y.¹ Chu, C.² Huang, A.³ Zhan, C.⁴ Ma, Y.⁵ Ma, C.⁶

46
- 0027769721
- J. R. Proudfoot, U. R. Patel, S. J. Campbell, J. Org. Chem. 1993, 58, 6996-7000.
- (1993) J. Org. Chem. , vol.58 , pp. 6996-7000
- Proudfoot, J.R.¹ Patel, U.R.² Campbell, S.J.³

47
- 11844268057
- For metal contamination that significantly affects the results of catalytic reactions, see: a)R. K. Arvela, N. E. Leadbeater, M. S. Sangi, V. A. Williams, P. Granados, R. D. Singer, J. Org. Chem. 2005, 70, 161-168
- (2005) J. Org. Chem. , vol.70 , pp. 161-168
- Arvela, R.K.¹ Leadbeater, N.E.² Sangi, M.S.³ Williams, V.A.⁴ Granados, P.⁵ Singer, R.D.⁶

48
- 70349951976
- S. L. Buchwald, C. Bolm, Angew. Chem. 2009, 121, 5694-5695
- (2009) Angew. Chem. , vol.121 , pp. 5694-5695
- Buchwald, S.L.¹ Bolm, C.²

49
- 70349783568
- Angew. Chem. Int. Ed. 2009, 48, 5586-5587.
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 5586-5587

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