SCOPUS 정보 검색 플랫폼

Volumn 11, Issue 9, 2013, Pages 1533-1536

Synthesis of 3,3-disubstituted oxindoles by one-pot integrated Brønsted base-catalyzed trichloroacetimidation of 3-hydroxyoxindoles and Brønsted acid-catalyzed nucleophilic substitution reaction

(3) Piemontesi, Cyril a Wang, Qian a Zhu, Jieping a

a EPFL (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL COMPOUNDS; SUBSTITUTION REACTIONS;

3-HYDROXYOXINDOLES; CATALYTIC AMOUNTS; DFT COMPUTATIONS; NUCLEOPHILIC SUBSTITUTION REACTIONS; ONE POT; OXINDOLES; TRICHLOROACETONITRILE;

REACTION INTERMEDIATES;

EID: 84875836336 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c2ob27196f Document Type: Article

Times cited : (42)

References (51)

1
- 0038392407
- C. Marti E. M. Carreira Eur. J. Org. Chem. 2003 2209 2219
- (2003) Eur. J. Org. Chem. , pp. 2209-2219
- Marti, C.¹ Carreira, E.M.²

2
- 36749025633
- C. V. Galliford K. A. Scheidt Angew. Chem., Int. Ed. 2007 46 8748 8758
- (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 8748-8758
- Galliford, C.V.¹ Scheidt, K.A.²

3
- 70449382104
- B. M. Trost M. K. Brennan Synthesis 2009 3003 3025
- (2009) Synthesis , pp. 3003-3025
- Trost, B.M.¹ Brennan, M.K.²

4
- 77954271846
- F. Zhou Y.-L. Liu J. Zhou Adv. Synth. Catal. 2010 352 1381 1407
- (2010) Adv. Synth. Catal. , vol.352 , pp. 1381-1407
- Zhou, F.¹ Liu, Y.-L.² Zhou, J.³

5
- 77955674388
- A. Millemaggi R. J. K. Taylor Eur. J. Org. Chem. 2010 4527 4547
- (2010) Eur. J. Org. Chem. , pp. 4527-4547
- Millemaggi, A.¹ Taylor, R.J.K.²

6
- 81855210999
- J. E. M. N. Klein R. J. K. Taylor Eur. J. Org. Chem. 2011 6821 6841
- (2011) Eur. J. Org. Chem. , pp. 6821-6841
- Klein, J.E.M.N.¹ Taylor, R.J.K.²

7
- 0001553596
- R. L. Hinman C. P. Bauman J. Org. Chem. 1964 29 2431 2437
- (1964) J. Org. Chem. , vol.29 , pp. 2431-2437
- Hinman, R.L.¹ Bauman, C.P.²

8
- 1942489302
- J. R. Fuchs R. L. Funk J. Am. Chem. Soc. 2004 126 5068 5069
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 5068-5069
- Fuchs, J.R.¹ Funk, R.L.²

9
- 14844363196
- J. R. Fuchs R. L. Funk Org. Lett. 2005 7 677 680
- (2005) Org. Lett. , vol.7 , pp. 677-680
- Fuchs, J.R.¹ Funk, R.L.²

10
- 34548825098
- For an enantioselective version, see
- S. Krishnan B. M. Stoltz Tetrahedron Lett. 2007 48 7571 7573
- (2007) Tetrahedron Lett. , vol.48 , pp. 7571-7573
- Krishnan, S.¹ Stoltz, B.M.²

11
- 70350014973
- S. Ma X. Han S. Krishnan S. C. Virgil B. M. Stoltz Angew. Chem., Int. Ed. 2009 48 8037 8041
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 8037-8041
- Ma, S.¹ Han, X.² Krishnan, S.³ Virgil, S.C.⁴ Stoltz, B.M.⁵

12
- 40749099452
- D. B. England G. Merey A. Padwa Heterocycles 2007 74 491 506
- (2007) Heterocycles , vol.74 , pp. 491-506
- England, D.B.¹ Merey, G.² Padwa, A.³

13
- 34848889987
- D. B. England G. Merey A. Padwa Org. Lett. 2007 9 3805 3807
- (2007) Org. Lett. , vol.9 , pp. 3805-3807
- England, D.B.¹ Merey, G.² Padwa, A.³

14
- 84862907571
- C. Guo J. Song J.-Z. Huang P.-H. Chen S.-W. Luo L.-Z. Gong Angew. Chem., Int. Ed. 2012 51 1046 1050
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 1046-1050
- Guo, C.¹ Song, J.² Huang, J.-Z.³ Chen, P.-H.⁴ Luo, S.-W.⁵ Gong, L.-Z.⁶

15
- 84863115507
- L. Song Q.-X. Guo X.-C. Li J. Tian Y.-G. Peng Angew. Chem., Int. Ed. 2012 51 1899 1902
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 1899-1902
- Song, L.¹ Guo, Q.-X.² Li, X.-C.³ Tian, J.⁴ Peng, Y.-G.⁵

16
- 84941944744
- H.-L. Wei T. Piou J. Dufour L. Neuville J. Zhu Org. Lett. 2011 13 2244 2247
- (2011) Org. Lett. , vol.13 , pp. 2244-2247
- Wei, H.-L.¹ Piou, T.² Dufour, J.³ Neuville, L.⁴ Zhu, J.⁵

17
- 77958175349
- S. Jaegli J.-P. Vors L. Neuville J. Zhu Tetrahedron 2010 66 8911 8921
- (2010) Tetrahedron , vol.66 , pp. 8911-8921
- Jaegli, S.¹ Vors, J.-P.² Neuville, L.³ Zhu, J.⁴

18
- 77952410686
- S. Jaegli W. Erb P. Retailleau J.-P. Vors L. Neuville J. Zhu Chem.-Eur. J. 2010 16 5863 5867
- (2010) Chem.-Eur. J. , vol.16 , pp. 5863-5867
- Jaegli, S.¹ Erb, W.² Retailleau, P.³ Vors, J.-P.⁴ Neuville, L.⁵ Zhu, J.⁶

19
- 77957856689
- S. Jaegli J. Dufour H.-L. Wei T. Piou X.-H. Duan J.-P. Vors L. Neuville J. Zhu Org. Lett. 2010 12 4498 4501
- (2010) Org. Lett. , vol.12 , pp. 4498-4501
- Jaegli, S.¹ Dufour, J.² Wei, H.-L.³ Piou, T.⁴ Duan, X.-H.⁵ Vors, J.-P.⁶ Neuville, L.⁷ Zhu, J.⁸

20
- 65249116566
- W. Erb L. Neuville J. Zhu J. Org. Chem. 2009 74 3109 3115
- (2009) J. Org. Chem. , vol.74 , pp. 3109-3115
- Erb, W.¹ Neuville, L.² Zhu, J.³

21
- 72049085540
- S. Jaegli J.-P. Vors L. Neuville J. Zhu Synlett 2009 2997 2999
- (2009) Synlett , pp. 2997-2999
- Jaegli, S.¹ Vors, J.-P.² Neuville, L.³ Zhu, J.⁴

22
- 33846425354
- A. Pinto Y. Jia L. Neuville J. Zhu Chem.-Eur. J. 2007 13 961 967
- (2007) Chem.-Eur. J. , vol.13 , pp. 961-967
- Pinto, A.¹ Jia, Y.² Neuville, L.³ Zhu, J.⁴

23
- 33749023851
- F. Bonnaterre M. Bois-Choussy J. Zhu Org. Lett. 2006 8 4351 4354
- (2006) Org. Lett. , vol.8 , pp. 4351-4354
- Bonnaterre, F.¹ Bois-Choussy, M.² Zhu, J.³

24
- 65549088656
- A. Pinto L. Neuville J. Zhu Tetrahedron Lett. 2009 50 3602 3605
- (2009) Tetrahedron Lett. , vol.50 , pp. 3602-3605
- Pinto, A.¹ Neuville, L.² Zhu, J.³

25
- 34250838053
- A. Pinto L. Neuville J. Zhu Angew. Chem., Int. Ed. 2007 46 3291 3295
- (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 3291-3295
- Pinto, A.¹ Neuville, L.² Zhu, J.³

26
- 33750346700
- A. Pinto L. Neuville P. Retailleau J. Zhu Org. Lett. 2006 8 4927 4930
- (2006) Org. Lett. , vol.8 , pp. 4927-4930
- Pinto, A.¹ Neuville, L.² Retailleau, P.³ Zhu, J.⁴

27
- 80054696871
- For recent examples see
- I. Gorokhovik L. Neuville J. Zhu Org. Lett. 2011 13 5536 5539
- (2011) Org. Lett. , vol.13 , pp. 5536-5539
- Gorokhovik, I.¹ Neuville, L.² Zhu, J.³

28
- 84863011225
- R. Niu J. Xiao T. Liang X. Li Org. Lett. 2012 14 676 679
- (2012) Org. Lett. , vol.14 , pp. 676-679
- Niu, R.¹ Xiao, J.² Liang, T.³ Li, X.⁴

29
- 84255169381
- F. Zhou Z.-Y. Cao J. Zhang H.-B. Yang J. Zhou Chem.-Asian J. 2012 7 233 241
- (2012) Chem.-Asian J. , vol.7 , pp. 233-241
- Zhou, F.¹ Cao, Z.-Y.² Zhang, J.³ Yang, H.-B.⁴ Zhou, J.⁵

30
- 84867336857
- The N-methyl-3-hydroxyoxindole was stable in the presence of TsOH, see note 23 of ref. 4b
- F. Zhu F. Zhou Z.-Y. Cao C. Wang Y.-X. Zhang C.-H. Wang J. Zhou Synthesis 2012 44 3129 3144
- (2012) Synthesis , vol.44 , pp. 3129-3144
- Zhu, F.¹ Zhou, F.² Cao, Z.-Y.³ Wang, C.⁴ Zhang, Y.-X.⁵ Wang, C.-H.⁶ Zhou, J.⁷

31
- 0025777180
- R. B. Labroo V. M. Labroo M. M. King L. A. Cohen J. Org. Chem. 1991 56 3637 3642
- (1991) J. Org. Chem. , vol.56 , pp. 3637-3642
- Labroo, R.B.¹ Labroo, V.M.² King, M.M.³ Cohen, L.A.⁴

32
- 35248823162
- C.-M. Cheung F. W. Goldberg P. Magnus C. J. Russell R. Turnbull V. Lynch J. Am. Chem. Soc. 2007 129 12320 12327
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 12320-12327
- Cheung, C.-M.¹ Goldberg, F.W.² Magnus, P.³ Russell, C.J.⁴ Turnbull, R.⁵ Lynch, V.⁶

33
- 0022636075
- R. R. Schmidt Angew. Chem., Int. Ed. Engl. 1986 25 212 235
- (1986) Angew. Chem., Int. Ed. Engl. , vol.25 , pp. 212-235
- Schmidt, R.R.¹

34
- 37049113139
- T. Iversen D. R. Bundle J. Chem. Soc., Chem. Commun. 1981 1240 1241
- (1981) J. Chem. Soc., Chem. Commun. , pp. 1240-1241
- Iversen, T.¹ Bundle, D.R.²

35
- 0036182789
- A. A.-H. Abdel-Rahman G. A. Winterfeld M. Takhi R. R. Schmidt Eur. J. Org. Chem. 2002 713 717
- (2002) Eur. J. Org. Chem. , pp. 713-717
- Abdel-Rahman, A.A.-H.¹ Winterfeld, G.A.² Takhi, M.³ Schmidt, R.R.⁴

36
- 2342509509
- I. A. I. Ali E. S. H. El Ashry R. R. Schmidt Tetrahedron 2004 60 4773 4780
- (2004) Tetrahedron , vol.60 , pp. 4773-4780
- Ali, I.A.I.¹ El Ashry, E.S.H.² Schmidt, R.R.³

37
- 33846599336
- C. Rondot P. Retailleau J. Zhu Org. Lett. 2007 9 247 250
- (2007) Org. Lett. , vol.9 , pp. 247-250
- Rondot, C.¹ Retailleau, P.² Zhu, J.³

38
- 84866927588
- S. Lin E. N. Jacobsen Nat. Chem. 2012 4 817 824
- (2012) Nat. Chem. , vol.4 , pp. 817-824
- Lin, S.¹ Jacobsen, E.N.²

39
- 33746315109
- J. Zhang R. R. Schmidt Synlett 2006 1729 1733
- (2006) Synlett , pp. 1729-1733
- Zhang, J.¹ Schmidt, R.R.²

40
- 78649532766
- Reaction of a trichloroimidate derivative of 6-chloro-3-phenyl-3-hydroxy- N-methyloxindole with H2O¹⁸ in the presence of diphenylphosphoric acid afforded a small amount of 3-hydroxylated derivative without incorporation of the O¹⁸ hydroxyl group
- A. Devineau G. Pousse C. Taillier J. Blanchet J. Rouden V. Dalla Adv. Synth. Catal. 2010 352 2881 2886
- (2010) Adv. Synth. Catal. , vol.352 , pp. 2881-2886
- Devineau, A.¹ Pousse, G.² Taillier, C.³ Blanchet, J.⁴ Rouden, J.⁵ Dalla, V.⁶

41
- 84856215640
- Computations were carried out using ADF2012 software
- T. Lu F. Chen J. Comput. Chem. 2012 33 580 592
- (2012) J. Comput. Chem. , vol.33 , pp. 580-592
- Lu, T.¹ Chen, F.²

42
- 20644438873
- G. Te Velde F. M. Bickelhaupt E. J. Baerends C. Fonseca Guerra S. J. A. van Gisbergen J. G. Snijders T. Ziegler J. Comput. Chem. 2001 22 931 967
- (2001) J. Comput. Chem. , vol.22 , pp. 931-967
- Te Velde, G.¹ Bickelhaupt, F.M.² Baerends, E.J.³ Fonseca Guerra, C.⁴ Van Gisbergen, S.J.A.⁵ Snijders, J.G.⁶ Ziegler, T.⁷

43
- 0032221816
- C. Fonseca Guerra J. G. Snijders G. Te Velde E. J. Baerends Theor. Chem. Acc. 1998 99 391 403
- (1998) Theor. Chem. Acc. , vol.99 , pp. 391-403
- Fonseca Guerra, C.¹ Snijders, J.G.² Te Velde, G.³ Baerends, E.J.⁴

44
- 7944235964
- Vrije Universiteit, Amsterdam, The Netherlands
- ADF2012, SCM, Theoretical Chemistry, Vrije Universiteit, Amsterdam, The Netherlands, http://www.scm.com
- ADF2012, SCM, Theoretical Chemistry

45
- 33751157732
- P. J. Stephens F. J. Devlin C. F. Chabalowski M. J. Frisch J. Phys. Chem. 1994 98 11623 11627
- (1994) J. Phys. Chem. , vol.98 , pp. 11623-11627
- Stephens, P.J.¹ Devlin, F.J.² Chabalowski, C.F.³ Frisch, M.J.⁴

46
- 4243553426
- A. D. Becke Phys. Rev. A 1988 38 3098 3100
- (1988) Phys. Rev. A , vol.38 , pp. 3098-3100
- Becke, A.D.¹

47
- 0345491105
- The participation of the pz orbital of the C-6 is 16.88% LOLπ is a function of the kinetic energy density which offers an intuitive depiction of a π-bond and detailed information on the nature and location of electron pairs.
- C. Lee W. Yang R. G. Parr Phys. Rev. B: Condens. Matter 1998 37 785 789
- (1998) Phys. Rev. B: Condens. Matter , vol.37 , pp. 785-789
- Lee, C.¹ Yang, W.² Parr, R.G.³

48
- 0034604357
- H. L. Schmider A. D. Becke J. Mol. Struct. (THEOCHEM) 2000 527 51 61
- (2000) J. Mol. Struct. (THEOCHEM) , vol.527 , pp. 51-61
- Schmider, H.L.¹ Becke, A.D.²

49
- 0037154598
- The different reactivity of 4-nitrophenyl triflate versus hard and soft nucleophiles is known, see
- H. L. Schmider A. D. Becke J. Chem. Phys. 2002 116 3184 3193
- (2002) J. Chem. Phys. , vol.116 , pp. 3184-3193
- Schmider, H.L.¹ Becke, A.D.²

50
- 0033214303
- L. Neuville A. Bigot M. E. Tran Huu Dau J. Zhu J. Org. Chem. 1999 64 7638 7642
- (1999) J. Org. Chem. , vol.64 , pp. 7638-7642
- Neuville, L.¹ Bigot, A.² Tran Huu Dau, M.E.³ Zhu, J.⁴

51
- 79957514567
- J.-I. Yoshida K. Saito T. Nokami A. Nagaki Synlett 2011 1189 1194
- (2011) Synlett , pp. 1189-1194
- Yoshida, J.-I.¹ Saito, K.² Nokami, T.³ Nagaki, A.⁴

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.