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Synlett

Volumn , Issue 3, 2007, Pages 419-422

A non-classical route to 2,3-diiodoindoles from indole-2-carboxylic acids

(3) Putey, Aurélien a Popowycz, Florence a Joseph, Benoît a

a UNIVERSITÉ LYON 1 (France)

Author keywords

2,3 diiodoindole; Decarboxylation; Iodination

Indexed keywords

2 INDOLECARBOXYLIC ACID; 2,3 DIIODOINDOLE DERIVATIVE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DECARBOXYLATION; IODINATION; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 33847366220 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-967953 Document Type: Article

Times cited : (13)

References (34)

1
- 0034605829
- Liu, Y.; Gribble, G. W. Tetrahedron Lett. 2000, 41, 8717.
- (2000) Tetrahedron Lett , vol.41 , pp. 8717
- Liu, Y.¹ Gribble, G.W.²

2
- 0013924939
- (a) Szmuszkovicz, J.; Glenn, E. M.; Heinzelman, R. V.; Hester, J. B. Jr.; Youngdale, G. A. J. Med. Chem. 1966, 9, 527.
- (1966) J. Med. Chem , vol.9 , pp. 527
- Szmuszkovicz, J.¹ Glenn, E.M.² Heinzelman, R.V.³ Hester Jr., J.B.⁴ Youngdale, G.A.⁵

3
- 0014044829
- (b) Glenn, E. M.; Bowman, B. J.; Kooyers, W.; Koslowske, T.; Myers, M. L. J. Pharmacol. Exp. Ther. 1967, 155, 157.
- (1967) J. Pharmacol. Exp. Ther , vol.155 , pp. 157
- Glenn, E.M.¹ Bowman, B.J.² Kooyers, W.³ Koslowske, T.⁴ Myers, M.L.⁵

4
- 0037201085
- (a) Liu, Y.; Gribble, G. W. Tetrahedron Lett. 2002, 43, 7135.
- (2002) Tetrahedron Lett , vol.43 , pp. 7135
- Liu, Y.¹ Gribble, G.W.²

5
- 2542569632
- (b) Yang, X.; Althammer, A.; Knochel, P. Org. Lett. 2004, 6, 1665.
- (2004) Org. Lett , vol.6 , pp. 1665
- Yang, X.¹ Althammer, A.² Knochel, P.³

6
- 18844440955
- (c) Baron, O.; Knochel, P. Angew. Chem. Int. Ed 2005, 44, 3133.
- (2005) Angew. Chem. Int. Ed , vol.44 , pp. 3133
- Baron, O.¹ Knochel, P.²

7
- 33750302489
- (d) Ueda, I.; Nishiura, M.; Takahashi, T.; Eda, K.; Hashimoto, M.; Yamamura, K. Tetrahedron Lett. 2006, 47, 8535.
- (2006) Tetrahedron Lett , vol.47 , pp. 8535
- Ueda, I.¹ Nishiura, M.² Takahashi, T.³ Eda, K.⁴ Hashimoto, M.⁵ Yamamura, K.⁶

8
- 0035897217
- (e) Liu, Y.; Gribble, G. W. Tetrahedron Lett. 2001, 42, 2949.
- (2001) Tetrahedron Lett , vol.42 , pp. 2949
- Liu, Y.¹ Gribble, G.W.²

9
- 0000916613
- (a) Erickson, K. L.; Brennan, M. R.; Namnum, P. A. Synth. Commun. 1981, 11, 253.
- (1981) Synth. Commun , vol.11 , pp. 253
- Erickson, K.L.¹ Brennan, M.R.² Namnum, P.A.³

10
- 0000916513
- (b) Brennan, M. R.; Erickson, K. L.; Szmalc, F. S.; Tansey, M. J.; Thornton, J. M. Heterocycles 1986, 24, 2879.
- (1986) Heterocycles , vol.24 , pp. 2879
- Brennan, M.R.¹ Erickson, K.L.² Szmalc, F.S.³ Tansey, M.J.⁴ Thornton, J.M.⁵

11
- 21144474496
- (c) Gribble, G. W.; Allison, B. D.; Conway, S. C.; Saulnier, M. G. Org. Prep. Proced. Int. 1992, 24, 649.
- (1992) Org. Prep. Proced. Int , vol.24 , pp. 649
- Gribble, G.W.¹ Allison, B.D.² Conway, S.C.³ Saulnier, M.G.⁴

12
- 33845553875
- Saulnier, M. G.; Gribble, G. W. J. Org. Chem. 1982, 47, 757.
- (1982) J. Org. Chem , vol.47 , pp. 757
- Saulnier, M.G.¹ Gribble, G.W.²

13
- 0009191318
- Katritzky, A. R.; Akutagawa, K. Tetrahedron Lett. 1985, 26, 5935.
- (1985) Tetrahedron Lett , vol.26 , pp. 5935
- Katritzky, A.R.¹ Akutagawa, K.²

14
- 0000771565
- Bergman, J.; Venemalm, L. J. Org. Chem. 1992, 57, 2495.
- (1992) J. Org. Chem , vol.57 , pp. 2495
- Bergman, J.¹ Venemalm, L.²

15
- 84989492823
- Bocchi, V.; Palla, G. Synthesis 1982, 1096.
- (1982) Synthesis , pp. 1096
- Bocchi, V.¹ Palla, G.²

16
- 0029823888
- Ezquerra, J.; Pedregal, C.; Lamas, C.; Barluenga, J.; Pérez, M.; García-Martín, M. A.; González, J. M. J. Org. Chem. 1996, 61, 5804.
- (1996) J. Org. Chem , vol.61 , pp. 5804
- Ezquerra, J.¹ Pedregal, C.² Lamas, C.³ Barluenga, J.⁴ Pérez, M.⁵ García-Martín, M.A.⁶ González, J.M.⁷

17
- 0032514835
- (a) Abell, A. D.; Nabbs, B. K.; Battersby, A. R. J. Org. Chem. 1998, 63, 8163.
- (1998) J. Org. Chem , vol.63 , pp. 8163
- Abell, A.D.¹ Nabbs, B.K.² Battersby, A.R.³

18
- 0347651908
- (b) Ono, N.; Yamamoto, T.; Shimada, N.; Kuroki, K.; Wada, M.; Utsunomiya, R.; Yano, T.; Uno, H.; Murashima, T. Heterocycles 2003, 61, 433.
- (2003) Heterocycles , vol.61 , pp. 433
- Ono, N.¹ Yamamoto, T.² Shimada, N.³ Kuroki, K.⁴ Wada, M.⁵ Utsunomiya, R.⁶ Yano, T.⁷ Uno, H.⁸ Murashima, T.⁹

19
- 0347419425
- (c) Skowronek, P.; Lightner, D. A. Monatsh. Chem. 2003, 134, 889.
- (2003) Monatsh. Chem , vol.134 , pp. 889
- Skowronek, P.¹ Lightner, D.A.²

20
- 0242660830
- (d) Tu, B.; Ghosh, B.; Lightner, D. A. J. Org. Chem. 2003, 68, 8950.
- (2003) J. Org. Chem , vol.68 , pp. 8950
- Tu, B.¹ Ghosh, B.² Lightner, D.A.³

21
- 0142042396
- (e) Heynderickx, A.; Mohamed Kaou, A.; Moustrou, C.; Samat, A.; Guglielmetti, R. New J. Chem. 2003, 27, 1425.
- (2003) New J. Chem , vol.27 , pp. 1425
- Heynderickx, A.¹ Mohamed Kaou, A.² Moustrou, C.³ Samat, A.⁴ Guglielmetti, R.⁵

22
- 0141631724
- (f) Hayashi, T.; Nakashima, Y.; Ito, K.; Ikegami, T.; Aritome, I.; Suzuki, A.; Hisaeda, Y. Org. Lett. 2003, 5, 2845.
- (2003) Org. Lett , vol.5 , pp. 2845
- Hayashi, T.¹ Nakashima, Y.² Ito, K.³ Ikegami, T.⁴ Aritome, I.⁵ Suzuki, A.⁶ Hisaeda, Y.⁷

23
- 2442428089
- (g) Tu, B.; Ghosh, B.; Lightner, D. A. Monatsh. Chem. 2004, 135, 519.
- (2004) Monatsh. Chem , vol.135 , pp. 519
- Tu, B.¹ Ghosh, B.² Lightner, D.A.³

24
- 33947320867
- Frydman, B.; Reil, S. J.; Boned, J.; Rapoport, H. J. Org. Chem. 1968, 33, 3762.
- (1968) J. Org. Chem , vol.33 , pp. 3762
- Frydman, B.¹ Reil, S.J.² Boned, J.³ Rapoport, H.⁴

25
- 9744285722
- Coowar, D.; Bouissac, J.; Hanbali, M.; Paschaki, M.; Mohier, E.; Luu, B. J. Med. Chem. 2004, 47, 6270.
- (2004) J. Med. Chem , vol.47 , pp. 6270
- Coowar, D.¹ Bouissac, J.² Hanbali, M.³ Paschaki, M.⁴ Mohier, E.⁵ Luu, B.⁶

26
- 33847352059
- Typical Procedure for Iodinative Decarboxylation: To a stirred solution of NaHCO3 (34 mg, 0.40 mmol) in H2O (1.5 mL) was added 1-(ethoxymethyl)-6-methoxy-1H-indole-2-carboxylic acid (1a; 50 mg, 0.20 mmol, The suspension was stirred until a homogenous solution was obtained. CHCl3 (1.5 mL) and iodine (102 mg, 0.40 mmol) were added and the dark purple mixture was stirred at 70°C for 4 h. The reaction mixture was diluted with H2O (10 mL) and CHCl3 (10 mL) and the organic layer was separated. The aqueous layer was extracted with CHCl 3 (2 x 10 mL, The combined organic extracts were washed with a sat. aq solution of Na2S2O3, dried over Na 2SO4 and evaporated in vacuo. The crude residue was purified by flash chromatography (PE-EtOAc, 95:5) to afford 2a (87 mg, 95, as an oil which crystallized at r.t; mp 81-82°C (EtOAc-PE, IR KBr, 30
- 2: C, 31.54; H, 2.87; N, 3.06. Found: C, 31.88; H, 3.00; N, 3.12.

27
- 0008319463
- Indole-2-carboxylic esters were either commercially available or easily synthesized by Hemetsberger synthesis starting from the corresponding aldehydes, according to experimental procedures reported in ref. 12. Compound 1e was prepared according to: Boger, D. L.; Cerbone, L. R.; Yohannes, D. J. Org. Chem. 1988, 53, 5163.
- Indole-2-carboxylic esters were either commercially available or easily synthesized by Hemetsberger synthesis starting from the corresponding aldehydes, according to experimental procedures reported in ref. 12. Compound 1e was prepared according to: Boger, D. L.; Cerbone, L. R.; Yohannes, D. J. Org. Chem. 1988, 53, 5163.

28
- 33847407031
- Analytical Data of Compound 2b: oil. IR (film, 3058, 2975, 1436, 1389, 1215, 1094 cm-1. 1H NMR (300 MHz, CDCl3, δ, 1.16 (t, J, 7.2 Hz, 3 H, CH3, 3.49 (q, J, 7.2 Hz, 2 H, CH2, 5.66 (s, 2 H, CH2, 7.19-7.24 (m, 2 H, H-5, H-6, 7.41-7.48 (m, 2 H, H-4, H-7, 13C NMR (75 MHz, CDCl 3, δ, 15.1 (CH3, 64.2 (CH2, 75.3 (C, 77.7 (CH2, 95.3 (C, 110.4 (CH, 121.6 (CH, 121.8 (CH, 123.5 (CH, 132.2 (C, 138.2 (C, MS ESI, m/z, 428 [M, H, Anal. Calcd for C11H11I2NO: C, 30.94; H, 2.60; N, 3.28. Found: C, 31.22; H, 2.65; N, 3.33
- 2NO: C, 30.94; H, 2.60; N, 3.28. Found: C, 31.22; H, 2.65; N, 3.33.

29
- 33847374176
- Analytical Data of Compound 2c: mp 93-94°C (EtOAc-PE, IR (KBr, 3020, 2973, 2837, 1602, 1575, 1500, 1459, 1426, 1388, 1251, 1176, 1086 cm-1. 1H NMR (300 MHz, CDCl3, δ, 1.15 (t, J, 7.2 Hz, 3 H, CH3, 3.48 (q, J, 7.2 Hz, 2 H, CH2, 3.94 (s, 3 H, OCH3, 5.62 (s, 2 H, CH2, 6.53-6.59 (m, 1 H, H-5, 7.12-7.14 (m, 2 H, H-6, H-7, 13C NMR (75 MHz, CDCl3, δ, 15.1 (CH3, 55.5 (OCH3, 64.1 (CH2, 68.5 (C, 78.2 (CH2, 95.6 (C, 101.5 (CH, 103.7 (CH, 120.8 (C, 124.2 (CH, 139.9 (C, 152.2 (C, MS ESI, m/z, 458 [M, H, Anal. Calcd for C12H13I 2NO2: C, 31.53; H, 2.87; N, 3.06. Found: C, 31.75; H, 2.71; N, 2.90
- 2: C, 31.53; H, 2.87; N, 3.06. Found: C, 31.75; H, 2.71; N, 2.90.

30
- 33847387081
- Analytical Data of Compound 2d: mp 89-91°C (EtOAc-PE, IR (KBr, 3063, 2978, 2836, 1613, 1489, 1445, 1429, 1208, 1101, 1085 cm -1. 1H NMR (300 MHz, CDCl3, δ, 1.15 (t, J, 7.2 Hz, 3 H, CH3, 3.47 (q, J, 7.2 Hz, 2 H, CH2, 3.89 (s, 3 H, OCH3, 5.61 (s, 2 H, CH2, 6.83-6.86 (m, 2 H, H-4, H-6, 7.36 (d, J, 9.4 Hz, 1 H, H-7, 13C NMR (75 MHz, CDCl3, δ, 15.1 (CH3, 55.9 (OCH3, 64.1 (CH2, 74.5 (C, 77.8 (CH2, 95.0 (C, 103.0 (CH, 111.4 (CH, 113.8 (CH, 132.5 (C, 133.2 (C, 155.7 (C, MS ESI, m/z, 458 [M, H, Anal. Calcd for C 12H13I2NO2: C, 31.53; H, 2.87; N, 3.06. Found: C, 31.40; H, 2.77; N, 3.11
- 2: C, 31.53; H, 2.87; N, 3.06. Found: C, 31.40; H, 2.77; N, 3.11.

31
- 33750524424
- Putey, A.; Fournet, G.; Joseph, B. Synlett 2006, 2755.
- (2006) Synlett , pp. 2755
- Putey, A.¹ Fournet, G.² Joseph, B.³

32
- 33847362680
- Analytical Data of Compound 2o: mp 93-95°C (EtOAc-PE, IR (KBr, 3056, 2985, 2827, 1619, 1569, 1488, 1445, 1431, 1169, 1093 cm -1. 1H NMR (300 MHz, CDCl3, δ, 3.85 (s, 3 H, OCH3, 4.85 (d, J, 4.7 Hz, 2 H, CH2, 4.94 (d, J, 17.1 Hz, 1 H, CH2, 5.19 (d, J, 10.2 Hz, 1 H, CH2, 5.82-5.94 (m, 1 H, CH, 6.72 (d, J, 1.9 Hz, 1 H, H-7, 6.80 (dd, J, 1.9, 8.9 Hz, 1 H, H-5, 7.28 (d, J, 8.9 Hz, 1 H, H-4, 13C NMR (75 MHz, CDCl3, δ, 51.3 (CH 2, 55.9 (OCH3, 72.2 (C, 92.6 (C, 93.9 (CH, 110.8 (CH, 117.4, CH2, 122.1 (CH, 126.4(C, 132.2 (CH, 138.0 (C, 157.2 (C, MS ESI, m/z, 440 [M, H, Anal. Calcd for C12H11I2NO: C, 32.83; H, 2.53; N, 3.19. Found: C, 32.86; H, 2.44; N, 3.08
- 2NO: C, 32.83; H, 2.53; N, 3.19. Found: C, 32.86; H, 2.44; N, 3.08.

33
- 33847411003
- Analytical Data of Compound 3o: mp 165-167°C (CHCl 3-Et2O, IR (KBr, 3014, 2957, 1730, 1620, 1405, 1090 cm-1. 1H NMR (300 MHz, DMSO-d6, δ, 3.55-3.66 (m, 2 H, CH2I, 3.86 (s, 3 H, OCH3, 4.14 (dd, J, 10.2, 12.8 Hz, 1 H, NCH2, 4.81 (dd, J, 3.3, 12.8 Hz, 1 H, NCH2, 4.86-4.94 (m, 1 H, CH, 6.90 (dd, J, 1.9, 8.9 Hz, 1 H, H-5, 7.14 (d, J, 1.9Hz, 1 H, H-7, 7.36 (d, J, 8.9 Hz, 1 H, H-4, 13C NMR (75 MHz, DMSO-d6, δ, 4.2 (CH2I, 44.9 (NCH2, 55.7 (OCH3, 68.4 (C, 75.4 (CH, 92.8 (CH, 114.1 (CH, 121.1 (C, 123.7 (CH, 124.6 (C, 137.4 (C, 157.6 (C, 159.7 (C, MS ESI, m/z, 484 [M, H, Anal. Calcd for C13H11I2NO3: C, 32.32; H, 2.30; N, 2.90. Found: C, 32.63; H, 2.27; N, 3.02
- 3: C, 32.32; H, 2.30; N, 2.90. Found: C, 32.63; H, 2.27; N, 3.02.

34
- 0036035973
- Wang, M.; Xu, X.-X.; Liu, Q.; Xiong, L.; Yang, B.; Gao, L.-X. Synth. Commun. 2002, 32, 3437.
- (2002) Synth. Commun , vol.32 , pp. 3437
- Wang, M.¹ Xu, X.-X.² Liu, Q.³ Xiong, L.⁴ Yang, B.⁵ Gao, L.-X.⁶

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