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Volumn , Issue 7, 2007, Pages 1037-1042

Synthesis of functionalized spiroheterocycles by sequential multicomponent reaction/metal-catalyzed carbocylizations from simple β-ketoesters and amides

(4) Habib Zahmani, Hadjira a Viala, Jacques b Hacini, Salih a Rodriguez, Jean b

a UNIVERSITY OF ORAN (Algeria)

b Institut Fresnel (France)

Author keywords

1,3 dicarbonyl compounds; Heck reaction; Multicomponent reactions; Ring closing metathesis; Spiroheterocycles

Indexed keywords

AMIDE; ESTER DERIVATIVE; HETEROCYCLIC COMPOUND; PALLADIUM;

ARTICLE; CARBOCYLIZATION; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; HECK REACTION; MULTICOMPONENT REACTION; POLYMERIZATION; RING CLOSING METATHESIS; STEREOCHEMISTRY;

EID: 34248166450 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-973896 Document Type: Article

Times cited : (30)

References (47)

1
- 84890597202
- For a recent monograph, see:, Zhu, J, Bienayme, H, Eds, Wiley-VCH: Weinheim
- (a) For a recent monograph, see: Multicomponent Reactions; Zhu, J.; Bienayme, H., Eds.; Wiley-VCH: Weinheim, 2005.
- (2005) Multicomponent Reactions

2
- 31544434530
- For some recent reviews on MCRs, see: b, and references cited therein
- For some recent reviews on MCRs, see: (b) Dömling, A. Chem. Rev. 2006, 106, 17; and references cited therein,
- (2006) Chem. Rev , vol.106 , pp. 17
- Dömling, A.¹

3
- 0034665244
- (c) Bienayme, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321.
- (2000) Chem. Eur. J , vol.6 , pp. 3321
- Bienayme, H.¹ Hulme, C.² Oddon, G.³ Schmitt, P.⁴

4
- 0001134412
- (d) Dömling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3168.
- (2000) Angew. Chem. Int. Ed , vol.39 , pp. 3168
- Dömling, A.¹ Ugi, I.²

5
- 0037391570
- (e) Zhu, J. Eur. J. Org. Chem. 2003, 1133.
- (2003) Eur. J. Org. Chem , pp. 1133
- Zhu, J.¹

6
- 0042745386
- (f) Orru, R. V.; de Greef, M. Synthesis 2003, 1471.
- (2003) Synthesis , pp. 1471
- Orru, R.V.¹ de Greef, M.²

7
- 17144366282
- (g) Ramon, D. J.; Yus, M. Angew. Chem. Int. Ed. 2005, 44, 1602.
- (2005) Angew. Chem. Int. Ed , vol.44 , pp. 1602
- Ramon, D.J.¹ Yus, M.²

8
- 7044235263
- For representative reviews, see: h
- For representative reviews, see: (h) Tietze, L. F. Chem. Rev. 1996, 96, 115.
- (1996) Chem. Rev , vol.96 , pp. 115
- Tietze, L.F.¹

9
- 0032087839
- (i) Tietze, L. F.; Lieb, M. E. Curr. Opin. Chem. Biol. 1998, 2, 363.
- (1998) Curr. Opin. Chem. Biol , vol.2 , pp. 363
- Tietze, L.F.¹ Lieb, M.E.²

10
- 0032953281
- (j) Rodriguez, J. Synlett 1999, 505.
- (1999) Synlett , pp. 505
- Rodriguez, J.¹

11
- 84890766709
- Wiley-VCH: Weinheim
- (k) Tietze, L. F.; Brasche, G.; Gericke, K. Domino Reactions in Organic Synthesis; Wiley-VCH: Weinheim, 2006.
- (2006) Domino Reactions in Organic Synthesis
- Tietze, L.F.¹ Brasche, G.² Gericke, K.³

12
- 0033019939
- Weber, L.; Illgen, M.; Almstetter, M. Synlett 1999, 366.
- (1999) Synlett , pp. 366
- Weber, L.¹ Illgen, M.² Almstetter, M.³

13
- 0034678033
- Schreiber, S. L. Science 2000, 287, 1964.
- (2000) Science , vol.287 , pp. 1964
- Schreiber, S.L.¹

14
- 0026418434
- (a) Trost, B. M. Science 1991, 254, 1471.
- (1991) Science , vol.254 , pp. 1471
- Trost, B.M.¹

15
- 0000591736
- (b) Trost, B. M. Angew. Chem. Int. Ed. 1995, 34, 258.
- (1995) Angew. Chem. Int. Ed , vol.34 , pp. 258
- Trost, B.M.¹

16
- 0036739952
- (c) Trost, B. M. Acc. Chem. Res. 2002, 35, 695.
- (2002) Acc. Chem. Res , vol.35 , pp. 695
- Trost, B.M.¹

17
- 0036291655
- (a) Wender, P. A.; Bi, F. C.; Gamber, G. G.; Gosselin, F.; Hubbard, R. D.; Scanio, M. J. C.; Sun, R.; Williams, T. J.; Zhang, L. Pure Appl. Chem. 2002, 74, 25.
- (2002) Pure Appl. Chem , vol.74 , pp. 25
- Wender, P.A.¹ Bi, F.C.² Gamber, G.G.³ Gosselin, F.⁴ Hubbard, R.D.⁵ Scanio, M.J.C.⁶ Sun, R.⁷ Williams, T.J.⁸ Zhang, L.⁹

18
- 0037313008
- (b) Wender, P. A.; Baryza, J. L.; Brenner, S. E.; Clarke, M. O.; Gamber, G. G.; Horan, J. C.; Jessop, T. C.; Kan, C.; Pattabiraman, K.; Williams, T. J. Pure Appl. Chem. 2003, 75, 143.
- (2003) Pure Appl. Chem , vol.75 , pp. 143
- Wender, P.A.¹ Baryza, J.L.² Brenner, S.E.³ Clarke, M.O.⁴ Gamber, G.G.⁵ Horan, J.C.⁶ Jessop, T.C.⁷ Kan, C.⁸ Pattabiraman, K.⁹ Williams, T.J.¹⁰

19
- 4644248644
- (c) Wender, P. A.; Baryza, J. L.; Brenner, S. E.; Clarke, M. O.; Craske, M. L.; Horan, J. C.; Meyer, T. Curr. Drug Discov. Technol. 2004, 1, 1.
- (2004) Curr. Drug Discov. Technol , vol.1 , pp. 1
- Wender, P.A.¹ Baryza, J.L.² Brenner, S.E.³ Clarke, M.O.⁴ Craske, M.L.⁵ Horan, J.C.⁶ Meyer, T.⁷

20
- 14844290896
- (d) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Pham, S. M.; Zhang, L. J. Am. Chem. Soc. 2005, 127, 2836.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 2836
- Wender, P.A.¹ Gamber, G.G.² Hubbard, R.D.³ Pham, S.M.⁴ Zhang, L.⁵

21
- 0002576569
- For a special issue in environmental chemistry, see
- For a special issue in environmental chemistry, see: Grissom, C. B. Chem. Rev. 1995, 95, 3.
- (1995) Chem. Rev , vol.95 , pp. 3
- Grissom, C.B.¹

22
- 0000851037
- Wender, P. A.; Handy, S. T.; Wright, D. L. Chem. Ind. (London) 1997, 765.
- (1997) Chem. Ind. (London) , pp. 765
- Wender, P.A.¹ Handy, S.T.² Wright, D.L.³

23
- 34248231128
- See refs 1a and 1b
- (a) See refs 1a and 1b.

24
- 23044473706
- (b) Gracias, V.; Gasiecki, A. F.; Djuric, S. W. Org. Lett. 2005, 7, 3183.
- (2005) Org. Lett , vol.7 , pp. 3183
- Gracias, V.¹ Gasiecki, A.F.² Djuric, S.W.³

25
- 11144310072
- For recent reviews, see: a
- For recent reviews, see: (a) Simon C., Constantieux T., Rodriguez J.; Eur. J. Org. Chem.; 2004, 4957.
- (2004) Eur. J. Org. Chem , pp. 4957
- Simon, C.¹ Constantieux, T.² Rodriguez, J.³

26
- 34248226233
- Attanasi, O. A, Spinelli, D, Eds, Societá Chimica Italiana: Rome
- (b) Constantieux, T.; Rodriguez, J. In Targets in Heterocyclic Systems, Vol 9; Attanasi, O. A.; Spinelli, D., Eds.; Societá Chimica Italiana: Rome, 2005.
- (2005) Targets in Heterocyclic Systems , vol.9
- Constantieux, T.¹ Rodriguez, J.²

27
- 33745775855
- (c) Liéby-Muller, F.; Simon, C.; Constantieux, T.; Rodriguez, J. QSAR Comb. Sci. 2006, 25, 432.
- (2006) QSAR Comb. Sci , vol.25 , pp. 432
- Liéby-Muller, F.¹ Simon, C.² Constantieux, T.³ Rodriguez, J.⁴

28
- 33746270208
- (a) Liéby-Muller, F.; Simon, C.; Imhof, K.; Constantieux, T.; Rodriguez, J. Synlett 2006, 1671.
- (2006) Synlett , pp. 1671
- Liéby-Muller, F.¹ Simon, C.² Imhof, K.³ Constantieux, T.⁴ Rodriguez, J.⁵

29
- 29044446242
- (b) Liéby-Muller, F.; Constantieux, T.; Rodriguez, J. J. Am. Chem. Soc. 2005, 127, 17176.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 17176
- Liéby-Muller, F.¹ Constantieux, T.² Rodriguez, J.³

30
- 0036418797
- (c) Habib-Zahmani, H.; Hacini, S.; Charonnet, E.; Rodriguez, J. Synlett 2002, 1827.
- (2002) Synlett , pp. 1827
- Habib-Zahmani, H.¹ Hacini, S.² Charonnet, E.³ Rodriguez, J.⁴

31
- 0033597970
- (a) Sannigrahi, M. Tetrahedron 1999, 55, 9007.
- (1999) Tetrahedron , vol.55 , pp. 9007
- Sannigrahi, M.¹

32
- 0012106210
- In Studies in Natural Products Chemistry
- Elsevier: Amsterdam
- (b) Martin, J. D. In Studies in Natural Products Chemistry, Vol. 6; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1990, 59.
- (1990) Atta-ur-Rahman, Ed , vol.6 , pp. 59
- Martin, J.D.¹

33
- 5644297236
- (c) El Bialy, S. A. A.; Braun, H.; Tietze, L. F. Synthesis 2004, 2249.
- (2004) Synthesis , pp. 2249
- El Bialy, S.A.A.¹ Braun, H.² Tietze, L.F.³

34
- 0035858744
- Takada, N.; Umemura, N.; Suenaga, K.; Chou, T.; Nagatsu, A.; Haino, T.; Yamada, K.; Uemura, D. Tetrahedron Lett. 2001, 42, 3491.
- (2001) Tetrahedron Lett , vol.42 , pp. 3491
- Takada, N.¹ Umemura, N.² Suenaga, K.³ Chou, T.⁴ Nagatsu, A.⁵ Haino, T.⁶ Yamada, K.⁷ Uemura, D.⁸

35
- 0035858695
- Takada, N.; Umemura, N.; Suenaga, K.; Uemura, D. Tetrahedron Lett. 2001, 42, 3495.
- (2001) Tetrahedron Lett , vol.42 , pp. 3495
- Takada, N.¹ Umemura, N.² Suenaga, K.³ Uemura, D.⁴

36
- 34248193708
- See ref. 10b
- (a) See ref. 10b.

37
- 0035036042
- (b) Charonnet, E.; Filippini, M. H.; Rodriguez, J. Synthesis 2001, 788.
- (2001) Synthesis , pp. 788
- Charonnet, E.¹ Filippini, M.H.² Rodriguez, J.³

38
- 34248232378
- General Procedure for MCRs: To a solution of ketoester or ketoamide 1 (1 mmol) and DBU (3 mmol) in appropriate solvent (4 mL, Table 1) was added the corresponding aldehyde 2 (1.1 mmol) and halide 3 (2 mmol, The resulting solution was stirred for the indicated time and at the indicated temperature (Table 1, After completion of the reaction and evaporation of most of the solvent under reduced pressure, 1 N solution of HCL (30 mL) was added to the oily residue. Extraction with Et2O (3 x 40 mL) followed by successive washing with distilled H2O (2 x 20 mL) and brine (20 mL) gave, after drying (MgSO4) and evaporation of the solvent, the crude compounds which were purified by flash chromatography on silica gel. Physical Data for Compound 4b: yellow oil; R f[Et2O-PE (50:50, 0.79. IR (liquid film, 2942, 1740, 1678, 1588, 1472, 1208, 1133, 927 cm-1. MS: m/z, 305 100, M
- 3): δ = 197.3, 168.9, 151.6, 144.7, 131.3, 132.0, 128.2, 118.8, 115.9, 120.1, 112.9, 115.5, 66.6, 60.4, 38.6, 32.7.

39
- 0038163433
- (a) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130.
- (1997) J. Am. Chem. Soc , vol.119 , pp. 9130
- Fürstner, A.¹ Langemann, K.²

40
- 0033612270
- (b) Cossy, J.; Bauer, D.; Bellosta, V. Tetrahedron Lett. 1999, 40, 4187.
- (1999) Tetrahedron Lett , vol.40 , pp. 4187
- Cossy, J.¹ Bauer, D.² Bellosta, V.³

41
- 0032566021
- (c) Ghosh, A. K.; Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 39, 4651.
- (1998) Tetrahedron Lett , vol.39 , pp. 4651
- Ghosh, A.K.¹ Cappiello, J.² Shin, D.³

42
- 0038163433
- (d) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130.
- (1997) J. Am. Chem. Soc , vol.119 , pp. 9130
- Fürstner, A.¹ Langemann, K.²

43
- 34248164881
- General Procedure for RCMs: To a 6 × 10-3 M solution of spiroheterocyclic precursors 4a-e in anhyd CH 2Cl2, under an atmosphere of argon, Grubbs' catalyst 5b was introduced in several portions of 2% every 2 h. The mixture was stirred at reflux and completion of reaction was checked by TLC. The mixture was filtered through a pad of silica gel and celite and the crude material was purified by flash chromatography on silica gel. Physical Data for Compound 6c: yellow solid; mp 104-106°C. IR (liquid film, 2960, 1708, 1620, 1460, 1201, 1030 cm-1. MS: m/z, 290 (100, M, H, 233 (17, 190 (5, 1H NMR (300.13 MHz, CDCl 3, β, 7.53 (d, J, 1.7 Hz, 1 H, 7.32 (s, 1 H, 6.67 (d, J, 3.3 Hz, 1 H, 6.49 (dd, J, 1.7, 3.3 Hz, 1 H, 5.75-5.85 (m, 2 H, 3.90-4.18 (m, 2 H, 3.81 (d, J, 11.7 Hz, 1 H, 3.03 (s, 3 H, 3.00 d, J, 11.7
- 3): δ = 198.6, 170.2, 151.8, 144.4, 127.7, 125.8, 128.4, 112.8, 115.5, 115.0, 60.4, 49.8, 38.9, 35.1, 31.9.

44
- 0000633011
- Vinyl Substitution with Organopalladium Intermediates
- Pergamon: Oxford
- Heck, R. F. Vinyl Substitution with Organopalladium Intermediates, In Comprehensive Organic Synthesis, Vol. 4; Pergamon: Oxford, 1991.
- (1991) Comprehensive Organic Synthesis , vol.4
- Heck, R.F.¹

45
- 0029743317
- (a) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215.
- (1996) J. Am. Chem. Soc , vol.118 , pp. 7215
- Wolfe, J.P.¹ Wagaw, S.² Buchwald, S.L.³

46
- 0033564994
- (b) Yang, B. H.; Buchwald, S. L. Org. Lett. 1999, 1, 35.
- (1999) Org. Lett , vol.1 , pp. 35
- Yang, B.H.¹ Buchwald, S.L.²

47
- 34248136833
- General Procedure for Heck Reaction: To a 4 × 10 -2 M solution of spiroheterocyclic precursors 4f and 4g in anhyd MeCN, under an atmosphere of argon, palladium acetate (4 equiv) and PPh3 (8 equiv) were added, followed by Et3N (1.2 equiv, The mixture was stirred at reflux and the completion of reaction was checked by TLC. The mixture was filtered through a pad of celite and the crude material was purified by flash chromatography on silica gel. Physical Data for Compound 7b: yellow powder; mp 169-171°C. IR (liquid film, 2926, 1719, 1626, 1444, 1337, 1256, 940 cm-1. MS: m/z, 326 (100, M, H, 295 (3, 255 (3, 201 (3, 164(16, 1H NMR (300.13 MHz, CDCl3, δ, 7.34-7.64 (m, 6 H, 5.41 (d, J, 0.9, 16.6 Hz, 2 H, 5.02 (d, J, 9.3 Hz, 1 H, 4.72 (dd, J, 1.1, 15.1 Hz, 2 H, 4.04 (dd, J =0.9, 11.3 Hz, 1 H, 3.57 d, J, 15
- 3): δ = 200.9, 169.0, 143.5, 141.8, 135.0, 130.5, 129.6, 129.5, 129.2, 128.8, 115.3, 112.8, 61.4, 54.2, 39.4, 37.1, 31.1.

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