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Synlett

Volumn , Issue 5, 2009, Pages 0727-0730

First example of C-3 alkylation of indoles with activated azetidines catalyzed by indium(III) bromide

(4) Yadav, J S a Subba Reddy, B V a Narasimhulu, G a Satheesh, G a

a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY (India)

Author keywords

Activated azetidine; C 3 alkylation; Indium(III) bromide; Indoles

Indexed keywords

EID: 62349140232 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087957 Document Type: Article

Times cited : (13)

References (39)

1
- 0003979828
- Academic Press: San Diego
- (a) Sundberg, R. J. Indoles; Academic Press: San Diego, 1996.
- (1996) Indoles
- Sundberg, R.J.¹

2
- 0035137292
- (b) Faulkner, D. J. Nat. Prod. Rep. 2001, 18, 1-49.
- (2001) Nat. Prod. Rep , vol.18 , pp. 1-49
- Faulkner, D.J.¹

3
- 0026769352
- (c) Ninomiya, I. J. Nat. Prod. 1992, 55, 541.
- (1992) J. Nat. Prod , vol.55 , pp. 541
- Ninomiya, I.¹

4
- 0001275286
- Katritzky, A. R, Rees, C. W, Scriven, E. F. V, Bird, C. W, Eds, Pergamon Press: Oxford
- (a) Sundberg, R. J. In Comprehensive Heterocyclic Chemistry II, Vol. 2; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V.; Bird, C. W., Eds.; Pergamon Press: Oxford, 1996, 207.
- (1996) Comprehensive Heterocyclic Chemistry II , vol.2 , pp. 207
- Sundberg, R.J.¹

5
- 0034740911
- (b) Gilchrist, T. L. J. Chem. Soc., Perkin Trans. 1 2001, 2491.
- (2001) J. Chem. Soc., Perkin Trans. 1 , pp. 2491
- Gilchrist, T.L.¹

6
- 0037366605
- (c) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893.
- (2003) Chem. Rev , vol.103 , pp. 893
- Horton, D.A.¹ Bourne, G.T.² Smythe, M.L.³

7
- 0038383709
- (d) Tois, J.; Franzen, R.; Koskinen, A. Tetrahedron 2003, 59, 5395.
- (2003) Tetrahedron , vol.59 , pp. 5395
- Tois, J.¹ Franzen, R.² Koskinen, A.³

8
- 1042276935
- (a) Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem. Int. Ed. 2004, 43, 550.
- (2004) Angew. Chem. Int. Ed , vol.43 , pp. 550
- Bandini, M.¹ Melloni, A.² Umani-Ronchi, A.³

9
- 0037138701
- (b) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 1172
- Austin, J.F.¹ MacMillan, D.W.C.²

10
- 0035825178
- (c) Jensen, K. B.; Thorhange, J.; Hazel, R. G.; Jorgensen, K. A. Angew. Chem. Int. Ed. 2001, 40, 160.
- (2001) Angew. Chem. Int. Ed , vol.40 , pp. 160
- Jensen, K.B.¹ Thorhange, J.² Hazel, R.G.³ Jorgensen, K.A.⁴

11
- 0037048689
- (a) Yoshiaki, N.; Masato, Y.; Youichi, I.; Masnobu, H.; Sakae, U. J. Am. Chem. Soc. 2002, 124, 11846.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 11846
- Yoshiaki, N.¹ Masato, Y.² Youichi, I.³ Masnobu, H.⁴ Sakae, U.⁵

12
- 0000478083
- (b) Wenkert, E.; Angell, E. C.; Ferreira, V. F.; Michelotti, E. L.; Piettre, S. R.; Sheu, J. H.; Swindell, C. S. J. Org. Chem. 1986, 51, 2343.
- (1986) J. Org. Chem , vol.51 , pp. 2343
- Wenkert, E.¹ Angell, E.C.² Ferreira, V.F.³ Michelotti, E.L.⁴ Piettre, S.R.⁵ Sheu, J.H.⁶ Swindell, C.S.⁷

13
- 19944413632
- (c) Bandini, M.; Melloni, A.; Tommasi, S.; Umani-Ronchi, A. Synlett 2005, 1199.
- (2005) Synlett , pp. 1199
- Bandini, M.¹ Melloni, A.² Tommasi, S.³ Umani-Ronchi, A.⁴

14
- 0037459683
- (a) Srivastava, N.; Banik, B. K. J. Org. Chem. 2003, 68, 2109.
- (2003) J. Org. Chem , vol.68 , pp. 2109
- Srivastava, N.¹ Banik, B.K.²

15
- 0037764697
- (b) Bartoli, G.; Bartolacci, M.; Bosco, M.; Foglia, G.; Giuliani, A.; Marcantoni, E.; Sambri, L.; Torregiani, E. J. Org. Chem. 2003, 68, 4594.
- (2003) J. Org. Chem , vol.68 , pp. 4594
- Bartoli, G.¹ Bartolacci, M.² Bosco, M.³ Foglia, G.⁴ Giuliani, A.⁵ Marcantoni, E.⁶ Sambri, L.⁷ Torregiani, E.⁸

16
- 0034752060
- (c) Yadav, J. S.; Abraham, S.; Reddy, B. V. S.; Sabitha, G. Synthesis 2001, 2165.
- (2001) Synthesis , pp. 2165
- Yadav, J.S.¹ Abraham, S.² Reddy, B.V.S.³ Sabitha, G.⁴

17
- 34248566934
- (d) Yadav, J. S.; Reddy, B. V. S.; Singh, A. P.; Basak, A. K. Tetrahedron Lett. 2007, 48, 4169.
- (2007) Tetrahedron Lett , vol.48 , pp. 4169
- Yadav, J.S.¹ Reddy, B.V.S.² Singh, A.P.³ Basak, A.K.⁴

18
- 0742286908
- (a) Campos, K. R.; Woo, J. C. S.; Lee, S.; Tillyer, R. D. Org. Lett. 2004, 6, 79.
- (2004) Org. Lett , vol.6 , pp. 79
- Campos, K.R.¹ Woo, J.C.S.² Lee, S.³ Tillyer, R.D.⁴

19
- 0346787850
- (b) Hong, K. B.; Lee, C. W.; Yum, E. K. Tetrahedron Lett. 2004, 45, 693.
- (2004) Tetrahedron Lett , vol.45 , pp. 693
- Hong, K.B.¹ Lee, C.W.² Yum, E.K.³

20
- 2542479631
- (c) Kohling, P.; Schmidt, A. M.; Eilbracht, P. Org. Lett. 2003, 5, 3213.
- (2003) Org. Lett , vol.5 , pp. 3213
- Kohling, P.¹ Schmidt, A.M.² Eilbracht, P.³

21
- 3142682149
- (d) Arcadi, A.; Bianchi, G.; Chiarini, M.; Anniballe, G.; Marinelli, F. Synlett 2004, 6, 944.
- (2004) Synlett , vol.6 , pp. 944
- Arcadi, A.¹ Bianchi, G.² Chiarini, M.³ Anniballe, G.⁴ Marinelli, F.⁵

22
- 34547482995
- (e) Yadav, J. S.; Reddy, B. V. S.; Aravind, S.; Narayana Kumar, G. G. K. S.; Srinivas Reddy, A. Tetrahedron Lett. 2007, 48, 6117.
- (2007) Tetrahedron Lett , vol.48 , pp. 6117
- Yadav, J.S.¹ Reddy, B.V.S.² Aravind, S.³ Narayana Kumar, G.G.K.S.⁴ Srinivas Reddy, A.⁵

23
- 0035888803
- (a) Nenajdenko, V. G.; Karpov, A. S.; Balenkova, E. S. Tetrahedron: Asymmetry 2001, 12, 2517.
- (2001) Tetrahedron: Asymmetry , vol.12 , pp. 2517
- Nenajdenko, V.G.¹ Karpov, A.S.² Balenkova, E.S.³

24
- 0037416880
- (b) Yadav, J. S.; Reddy, B. V. S.; Satheesh, G.; Prabhakar, A.; Kunwar, A. C. Tetrahedron Lett. 2003, 44, 2221.
- (2003) Tetrahedron Lett , vol.44 , pp. 2221
- Yadav, J.S.¹ Reddy, B.V.S.² Satheesh, G.³ Prabhakar, A.⁴ Kunwar, A.C.⁵

25
- 0037127509
- (c) Yadav, J. S.; Reddy, B. V. S.; Abraham, S.; Sabitha, G. Tetrahedron Lett. 2002, 43, 1565.
- (2002) Tetrahedron Lett , vol.43 , pp. 1565
- Yadav, J.S.¹ Reddy, B.V.S.² Abraham, S.³ Sabitha, G.⁴

26
- 1842635726
- (d) Yadav, J. S.; Reddy, B. V. S.; Satheesh, G. Tetrahedron Lett. 2004, 45, 3673.
- (2004) Tetrahedron Lett , vol.45 , pp. 3673
- Yadav, J.S.¹ Reddy, B.V.S.² Satheesh, G.³

27
- 62349120312
- (a) Zang, Z. H. Synlett 2005, 711.
- (2005) Synlett , pp. 711
- Zang, Z.H.¹

28
- 23844544537
- (b) Sakai, N.; Hirasawa, M.; Konakahara, T. Tetrahedron Lett. 2005, 46, 6407.
- (2005) Tetrahedron Lett , vol.46 , pp. 6407
- Sakai, N.¹ Hirasawa, M.² Konakahara, T.³

29
- 0041336703
- (a) Agnusdei, M.; Bandini, M.; Melloni, A.; Umani-Ronchi, A. J. Org. Chem. 2003, 68, 7126.
- (2003) J. Org. Chem , vol.68 , pp. 7126
- Agnusdei, M.¹ Bandini, M.² Melloni, A.³ Umani-Ronchi, A.⁴

30
- 34147109658
- (b) Huang, J.-M.; Wong, C.-M.; Xu, F.-X.; Loh, T.-P. Tetrahedron Lett. 2007, 48, 3375.
- (2007) Tetrahedron Lett , vol.48 , pp. 3375
- Huang, J.-M.¹ Wong, C.-M.² Xu, F.-X.³ Loh, T.-P.⁴

31
- 33847142253
- (c) Harada, S.; Takita, R.; Ohshima, T.; Matsunaga, S.; Shibasaki, M. Chem. Commun. 2007, 948.
- (2007) Chem. Commun , pp. 948
- Harada, S.¹ Takita, R.² Ohshima, T.³ Matsunaga, S.⁴ Shibasaki, M.⁵

32
- 0242467745
- (a) Yadav, J. S.; Reddy, B. V. S.; Rao, K. V.; Raj, K. S.; Prasad, A. R.; Kumar, S. K.; Kunwar, A. C.; Jayaprakash, P. J.; Jagannath, B. Angew. Chem. Int. Ed. 2003, 42, 5198.
- (2003) Angew. Chem. Int. Ed , vol.42 , pp. 5198
- Yadav, J.S.¹ Reddy, B.V.S.² Rao, K.V.³ Raj, K.S.⁴ Prasad, A.R.⁵ Kumar, S.K.⁶ Kunwar, A.C.⁷ Jayaprakash, P.J.⁸ Jagannath, B.⁹

33
- 0002484817
- (b) Yadav, J. S.; Reddy, B. V. S.; Kumar, G. M. Synlett 2001, 1781.
- (2001) Synlett , pp. 1781
- Yadav, J.S.¹ Reddy, B.V.S.² Kumar, G.M.³

34
- 0037289005
- (c) Yadav, J. S.; Reddy, B. V. S.; Baishya, G. Synlett 2003, 396.
- (2003) Synlett , pp. 396
- Yadav, J.S.¹ Reddy, B.V.S.² Baishya, G.³

35
- 0347949534
- (d) Yadav, J. S.; Reddy, B. V. S.; Swamy, T. Synthesis 2004, 106.
- (2004) Synthesis , pp. 106
- Yadav, J.S.¹ Reddy, B.V.S.² Swamy, T.³

36
- 0037629649
- (a) Yadav, J. S.; Reddy, B. V. S.; Krishna, A. D.; Swamy, T. Tetrahedron Lett. 2003, 44, 6055.
- (2003) Tetrahedron Lett , vol.44 , pp. 6055
- Yadav, J.S.¹ Reddy, B.V.S.² Krishna, A.D.³ Swamy, T.⁴

37
- 0345255613
- (b) Yadav, J. S.; Reddy, B. V. S.; Gakul, B. Green Chem. 2003, 5, 264.
- (2003) Green Chem , vol.5 , pp. 264
- Yadav, J.S.¹ Reddy, B.V.S.² Gakul, B.³

38
- 0242571933
- (c) Yadav, J. S.; Reddy, B. V. S.; Reddy, M. S.; Parimala, G. Synthesis 2003, 2390.
- (2003) Synthesis , pp. 2390
- Yadav, J.S.¹ Reddy, B.V.S.² Reddy, M.S.³ Parimala, G.⁴

39
- 62349132004
- General Procedure To a stirred solution of indole (1 mmol) in DCE (3 mL) were added the N-tosylazetidine (1 mmol) and InBr3 (0.1 mmol, The resulting mixture was stirred at reflux temperature for the appropriate time (Table 1, After complete conversion as indicated by TLC, the solvent was removed by evaporation, and the residue was diluted with H 2O and extracted with EtOAc (2 x 10 mL, The combined organic layers were dried over anhyd Na2SO4 and concentrated in vacuo. The resulting product was purified by column chromatography on SiO2 (Merck, 100-200 mesh) using EtOAc-hexane (3:7) as eluent to afford pure 3-alkenyl indole derivative. Spectroscopic Data for Selected Products N-1-[3-(1H-3-indolyl)propyl]-4-methyl-1- benzenesulfonamide (3a) Semisolid. IR KBr, νmax, 3405, 3054, 2923, 2853, 1598, 1455, 1322, 1156, 1091, 813, 771, 745 cm-1. 1H N
- 2NaS: 441.1612; found: 441.1619.

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