SCOPUS 정보 검색 플랫폼

Volumn , Issue 20, 2007, Pages 3123-3126

One-pot synthesis of 2H-chromene derivatives from ortho-naphthoquinones

(8) Da Silva, Fernando De C a Jorqueira, Alessandra a Gouvea R M a De Souza, Maria C B V a Howie, R Alan b Wardell, James L a Wardell, Solange M S V c Ferreira, Vitor F a

a FLUMINENSE FEDERAL UNIVERSITY (Brazil)

b UNIVERSITY OF ABERDEEN (United Kingdom)

c Medicamentos Farmanguinhos (Brazil)

Author keywords

Chromenes; Naphthoquinones; One pot cyclisation; Wittig reaction

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; 2H CHROMENE DERIVATIVE; CHLOROFORM; CHROMENE DERIVATIVE; HYDROGEN; PHOSPHONIUM DERIVATIVE; SODIUM HYDROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE; ONE POT SYNTHESIS; ROOM TEMPERATURE; WITTIG REACTION; X RAY CRYSTALLOGRAPHY;

EID: 37749037155 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-990925 Document Type: Article

Times cited : (12)

References (49)

1
- 0003607021
- McKillop, A, Ed, Elsevier Publishing Co, Amsterdam
- Katrikzy, A. R.; Rees, C. W.; Scriven, E. F. V. In Comprehensive Heterocyclic Chemistry II, Vol. 5; McKillop, A., Ed.; Elsevier Publishing Co.: Amsterdam, 1996.
- (1996) Comprehensive Heterocyclic Chemistry II , vol.5
- Katrikzy, A.R.¹ Rees, C.W.² Scriven, E.F.V.³

2
- 0036111256
- Bukuru, J. F.; Van Tuyen, N.; Van Puyvelde, L.; Mathenge, S. G.; Mudida, F. P.; De Kimpe, N. J. Nat. Prod. 2002, 65, 783.
- (2002) J. Nat. Prod , vol.65 , pp. 783
- Bukuru, J.F.¹ Van Tuyen, N.² Van Puyvelde, L.³ Mathenge, S.G.⁴ Mudida, F.P.⁵ De Kimpe, N.⁶

3
- 0028934337
- BenliSmane, A. F.; Ponchus, Y. F.; Verbist, J. F.; Petit, J.-Y.; Brion, J. D.; Welin, L. J. Clin. Pharmacol. 1995, 35, 298.
- (1995) Clin. Pharmacol , vol.35 , pp. 298
- BenliSmane, A.F.¹ Ponchus, Y.F.² Verbist, J.F.³ Petit, J.-Y.⁴ Brion, J.D.⁵ Welin, L.J.⁶

4
- 0030272214
- (a) Engler, T. A.; LaTessa, K. O.; Iyengar, R.; Chai, W. Y.; Agrios, K. Bioorg. Med. Chem. 1996, 4, 1755.
- (1996) Bioorg. Med. Chem , vol.4 , pp. 1755
- Engler, T.A.¹ LaTessa, K.O.² Iyengar, R.³ Chai, W.Y.⁴ Agrios, K.⁵

5
- 37749012434
- (b) Yamagishi, T.; Fujioka, T.; Mihashi, K.; Mizuki, K.; Cosentino, L. M.; Fowke, K.; Morris-Natschke, S. L.; Lee, K. H. Tetrahedron 2001, 57, 1559.
- (2001) Tetrahedron , vol.57 , pp. 1559
- Yamagishi, T.¹ Fujioka, T.² Mihashi, K.³ Mizuki, K.⁴ Cosentino, L.M.⁵ Fowke, K.⁶ Morris-Natschke, S.L.⁷ Lee, K.H.⁸

6
- 23944522335
- (a) Kidwai, M.; Saxena, S.; Khan, M. K. R.; Thukral, S. S. Bioorg. Med. Chem. Lett. 2005, 15, 4295.
- (2005) Bioorg. Med. Chem. Lett , vol.15 , pp. 4295
- Kidwai, M.¹ Saxena, S.² Khan, M.K.R.³ Thukral, S.S.⁴

7
- 0036754283
- (b) Khafagy, M. M.; Abd El-Wahab, A. H. F.; Eid, F. A.; El-Agrody, A. M. Farmaco 2002, 57, 715.
- (2002) Farmaco , vol.57 , pp. 715
- Khafagy, M.M.¹ Abd El-Wahab, A.H.F.² Eid, F.A.³ El-Agrody, A.M.⁴

8
- 0033799436
- For the preparation of cordiachromene, see: a
- For the preparation of cordiachromene, see: (a) Bouzbouz, S.; Goujon, J. Y.; Deplanne, J.; Kirschleger, B. Eur. J. Org. Chem. 2000, 3223.
- (2000) Eur. J. Org. Chem , pp. 3223
- Bouzbouz, S.¹ Goujon, J.Y.² Deplanne, J.³ Kirschleger, B.⁴

9
- 0034674413
- (b) Goujon, J. Y.; Zammattio, F.; Kirschleger, B. Tetrahedron: Asymmetry 2000, 11, 2409.
- (2000) Tetrahedron: Asymmetry , vol.11 , pp. 2409
- Goujon, J.Y.¹ Zammattio, F.² Kirschleger, B.³

10
- 0033550229
- (c) Kahn, P. H.; Cossy, J. Tetrahedron Lett. 1999, 40, 8113.
- (1999) Tetrahedron Lett , vol.40 , pp. 8113
- Kahn, P.H.¹ Cossy, J.²

11
- 37749031945
- Ferreira, V. F.; Pinto, A. V.; Coutada, L. C. M. Ann. Acad. Brasil. Cienc 1980, 52, 478.
- (1980) Ann. Acad. Brasil. Cienc , vol.52 , pp. 478
- Ferreira, V.F.¹ Pinto, A.V.² Coutada, L.C.M.³

12
- 2742584979
- Yavari, I.; Ramazani, A. J. Chem. Res., Synop. 1996, 382.
- (1996) J. Chem. Res., Synop , pp. 382
- Yavari, I.¹ Ramazani, A.²

13
- 0042624714
- (a) Hekmatshoar, R.; Souri, S.; Faridbod, F. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178, 1457.
- (2003) Phosphorus, Sulfur Silicon Relat. Elem , vol.178 , pp. 1457
- Hekmatshoar, R.¹ Souri, S.² Faridbod, F.³

14
- 37049090135
- (b) Nicolaides, D. N.; Lefkaditis, D. A.; Lianis, P. S.; Litinas, K. S. J. Chem. Soc., Perkin Trans. 1 1989, 2329.
- (1989) J. Chem. Soc., Perkin Trans. 1 , pp. 2329
- Nicolaides, D.N.¹ Lefkaditis, D.A.² Lianis, P.S.³ Litinas, K.S.⁴

15
- 37049071889
- (c) Nicolaides, D. N.; Adamopoulos, S. G.; Hatzigrigorioub, E. J.; Litinas, K. E. J. Chem. Soc., Perkin Trans. 1 1991, 3159.
- (1991) J. Chem. Soc., Perkin Trans. 1 , pp. 3159
- Nicolaides, D.N.¹ Adamopoulos, S.G.² Hatzigrigorioub, E.J.³ Litinas, K.E.⁴

16
- 0035996260
- (d) Nicolaides, D. N.; Gautam, D. R.; Litinas, K. E.; Papamehael, T. J. Chem. Soc., Perkin Trans. 1 2002, 1455.
- (2002) J. Chem. Soc., Perkin Trans. 1 , pp. 1455
- Nicolaides, D.N.¹ Gautam, D.R.² Litinas, K.E.³ Papamehael, T.⁴

17
- 0000114501
- (a) Kumar, P.; Bodas, M. S. Org. Lett. 2000, 2, 3821.
- (2000) Org. Lett , vol.2 , pp. 3821
- Kumar, P.¹ Bodas, M.S.²

18
- 37049068791
- (b) Nicolaides, D. N.; Litinas, K. E.; Lefkaditas, D. A.; Adamopoulos, S. G.; Raptopoulou, C. P.; Terzis, A. J. Chem. Soc., Perkin Trans. 1 1994, 2107.
- (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 2107
- Nicolaides, D.N.¹ Litinas, K.E.² Lefkaditas, D.A.³ Adamopoulos, S.G.⁴ Raptopoulou, C.P.⁵ Terzis, A.⁶

19
- 37049080479
- and earlier articles
- (c) Nicolaides, D. N.; Adamopoulos, S. G.; Lefkaditas, D. A.; Litinas, K. E. J. Chem. Soc., Perkin Trans. 1 1992, 2479; and earlier articles.
- (1992) J. Chem. Soc., Perkin Trans. 1 , pp. 2479
- Nicolaides, D.N.¹ Adamopoulos, S.G.² Lefkaditas, D.A.³ Litinas, K.E.⁴

20
- 3242878142
- (d) Boulos, L. S.; Elrahman, N. M. A. Phosphorus, Sulfur Silicon Relat. Elem. 1992, 68, 241.
- (1992) Phosphorus, Sulfur Silicon Relat. Elem , vol.68 , pp. 241
- Boulos, L.S.¹ Elrahman, N.M.A.²

21
- 0006595380
- Fieser, L. F. J. Am. Chem. Soc. 1926, 48, 2922.
- (1926) J. Am. Chem. Soc , vol.48 , pp. 2922
- Fieser, L.F.¹

22
- 37049177180
- (a) Hooker, S. C. J. Chem. Soc. 1892, 611.
- (1892) J. Chem. Soc , pp. 611
- Hooker, S.C.¹

23
- 0037249112
- (b) Pérez-Sacau, E.; Estévez-Braun, A.; Ravelo, A.; Ferro, E. A.; Tokuda, H.; Mukainakac, T.; Nishino, H. Bioorg. Med. Chem. 2003, 11, 483.
- (2003) Bioorg. Med. Chem , vol.11 , pp. 483
- Pérez-Sacau, E.¹ Estévez-Braun, A.² Ravelo, A.³ Ferro, E.A.⁴ Tokuda, H.⁵ Mukainakac, T.⁶ Nishino, H.⁷

24
- 16844370826
- (c) Pérez-Sacau, E.; Estévez-Braun, A.; Ravelo, A.; Yapu, D. G.; Turba, A. G. Chem. Biodivers. 2005, 2, 264.
- (2005) Chem. Biodivers , vol.2 , pp. 264
- Pérez-Sacau, E.¹ Estévez-Braun, A.² Ravelo, A.³ Yapu, D.G.⁴ Turba, A.G.⁵

25
- 0345662992
- Fieser, L. F.; Fieser, M. J. Am. Chem. Soc. 1948, 70, 3215.
- (1948) J. Am. Chem. Soc , vol.70 , pp. 3215
- Fieser, L.F.¹ Fieser, M.²

26
- 0032746858
- Alves, G. B. C.; Lopes, R. S. C.; Lopes, C. C.; Snieckus, V. Synthesis 1999, 1875.
- (1999) Synthesis , pp. 1875
- Alves, G.B.C.¹ Lopes, R.S.C.² Lopes, C.C.³ Snieckus, V.⁴

27
- 0037969038
- Reibenspies, J. H.; Willams, H. J.; Ortiz, C.; Scout, A. I.; Suarez, M.; Dominguez, X. A. J. Crystallogr. Spectrosc. Res. 1989, 19, 597.
- (1989) J. Crystallogr. Spectrosc. Res , vol.19 , pp. 597
- Reibenspies, J.H.¹ Willams, H.J.² Ortiz, C.³ Scout, A.I.⁴ Suarez, M.⁵ Dominguez, X.A.⁶

28
- 37749026513
- Data was obtained at 120 K with Mo KGk-α radiation by means of the Enraf Nonius KappaCCD area detector diffractometer of the EPSRC crystallographic service, based at the University of Southampton. Data collection was carried out under the control of the program COLLECT17a and data reduction and unit cell refinement were achieved with the COLLECT17a and DENZO programs.17b Correction for absorption, by comparison of the intensities of equivalent reflections, was applied using the program SADABS.17c The program ORTEP-3 for Windows17d was used in the preparation of Figure 3 and SHELXL-9717e and PLATON17f in the calculation of molecular geometry. The structure was solved by direct methods using SHELXS-9717g and fully refined by means of the program SHELXL-97.17e In the final stages of refinement, hydrogen atoms were introduced in calculated positions and refined with a riding model
- 17e In the final stages of refinement, hydrogen atoms were introduced in calculated positions and refined with a riding model.

29
- 0004281430
- Nonius BV: Delft, The Netherlands
- (a) Hooft, R. W. W. COLLECT; Nonius BV: Delft / The Netherlands, 1998.
- (1998) COLLECT
- Hooft, R.W.W.¹

30
- 0031059866
- Carter, C. W. Jr, Sweet, R. M, Eds, Academic Press: New York
- (b) Otwinowski, Z.; Minor, W. Methods in Enzymology, Macromolecular Crystallography, Part A, Vol. 276; Carter, C. W. Jr.; Sweet, R. M., Eds.; Academic Press: New York, 1997, 307.
- (1997) Methods in Enzymology, Macromolecular Crystallography, Part A , vol.276 , pp. 307
- Otwinowski, Z.¹ Minor, W.²

31
- 37749009472
- Sheldrick, G. M. SADABS, Version 2.10, Bruker AXS Inc, Madison, Wisconsin, USA, 2003
- (c) Sheldrick, G. M. SADABS, Version 2.10.; Bruker AXS Inc.: Madison / Wisconsin / USA, 2003.

32
- 0141452964
- (d) Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837.
- (1999) J. Appl. Crystallogr , vol.32 , pp. 837
- Farrugia, L.J.¹

33
- 0004150157
- University of Göttingen: Germany
- (e) Sheldrick, G. M. SHELXL-97: Program for Crystal Structure Refinement; University of Göttingen: Germany, 1997.
- (1997) SHELXL-97: Program for Crystal Structure Refinement
- Sheldrick, G.M.¹

34
- 0001792356
- (f) Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7.
- (2003) J. Appl. Crystallogr , vol.36 , pp. 7
- Spek, A.L.¹

35
- 0004150157
- University of Göttingen: Germany
- (g) Sheldrick, G. M. SHELXS-97: Program for the Solution of Crystal Structures; University of Göttingen: Germany, 1997.
- (1997) SHELXS-97: Program for the Solution of Crystal Structures
- Sheldrick, G.M.¹

36
- 37749051964
- 3. CCDC deposition no: 292382.
- 3. CCDC deposition no: 292382.

37
- 0029360394
- (a) Li, C. J.; Wang, C.; Pardee, B. A. Cancer Res. 1995, 55, 3712.
- (1995) Cancer Res , vol.55 , pp. 3712
- Li, C.J.¹ Wang, C.² Pardee, B.A.³

38
- 0036348011
- (b) Pardee, A. B.; Li, Y. Z.; Li, C. J. Curr. Cancer Drug Targets 2002, 2, 227.
- (2002) Curr. Cancer Drug Targets , vol.2 , pp. 227
- Pardee, A.B.¹ Li, Y.Z.² Li, C.J.³

39
- 0033276625
- (c) Huang, L. L.; Pardee, A. B. Mol. Med. 1999, 5, 711.
- (1999) Mol. Med , vol.5 , pp. 711
- Huang, L.L.¹ Pardee, A.B.²

40
- 0027377069
- (d) Li, C. J.; Averboukh, L.; Pardee, A. B. J. Biol. Chem. 1993, 268, 22463.
- (1993) J. Biol. Chem , vol.268 , pp. 22463
- Li, C.J.¹ Averboukh, L.² Pardee, A.B.³

41
- 17544391279
- (e) Frydman, B.; Marton, L. J.; Sun, S. J.; Neder, K.; Witiak, T. D.; Liu, A. A.; Wang, H. M.; Mao, Y.; Wu, H. Y.; Sanders, M. M.; Liu, L. F. Cancer Res. 1997, 57, 620.
- (1997) Cancer Res , vol.57 , pp. 620
- Frydman, B.¹ Marton, L.J.² Sun, S.J.³ Neder, K.⁴ Witiak, T.D.⁵ Liu, A.A.⁶ Wang, H.M.⁷ Mao, Y.⁸ Wu, H.Y.⁹ Sanders, M.M.¹⁰ Liu, L.F.¹¹

42
- 0033539487
- (f) Li, C. J.; Li, Y.-Z.; Pinto, A. V.; Pardee, A. B. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 13369.
- (1999) Proc. Natl. Acad. Sci. U.S.A , vol.96 , pp. 13369
- Li, C.J.¹ Li, Y.-Z.² Pinto, A.V.³ Pardee, A.B.⁴

43
- 0038381447
- (a) da Silva, M. N.; Ferreira, V. F.; de Souza, M. C. B. V. Quim. Nova 2003, 26, 407.
- (2003) Quim. Nova , vol.26 , pp. 407
- da Silva, M.N.¹ Ferreira, V.F.² de Souza, M.C.B.V.³

44
- 0035223367
- (b) Dubin, M.; Fernadez-Villamil, S. H.; Stoppani, A. O. Medicina 2001, 61, 343.
- (2001) Medicina , vol.61 , pp. 343
- Dubin, M.¹ Fernadez-Villamil, S.H.² Stoppani, A.O.³

45
- 33745626156
- (a) Ferreira, V. F.; Jorqueira, A.; Souza, A. M. T.; da Silva, M. N.; de Souza, M. C. B. V.; Gouvêa, R. M.; Rodrigues, C. R.; Pinto, A. V.; Castro, H. C.; Santos, D. O.; Araujo, H. P.; Bourguignon, S. C. Bioorg. Med. Chem. 2006, 14, 5459.
- (2006) Bioorg. Med. Chem , vol.14 , pp. 5459
- Ferreira, V.F.¹ Jorqueira, A.² Souza, A.M.T.³ da Silva, M.N.⁴ de Souza, M.C.B.V.⁵ Gouvêa, R.M.⁶ Rodrigues, C.R.⁷ Pinto, A.V.⁸ Castro, H.C.⁹ Santos, D.O.¹⁰ Araujo, H.P.¹¹ Bourguignon, S.C.¹²

46
- 27544503549
- (b) Barbosa, T. P.; Camara, C. A.; Silva, T. M. S.; Martins, R. M.; Pinto, A. V.; Vargas, M. D. Bioorg. Med. Chem. 2005, 13, 6464.
- (2005) Bioorg. Med. Chem , vol.13 , pp. 6464
- Barbosa, T.P.¹ Camara, C.A.² Silva, T.M.S.³ Martins, R.M.⁴ Pinto, A.V.⁵ Vargas, M.D.⁶

47
- 9644291550
- (c) Silva, T. M. S.; Camara, C. A.; Barbosa, T. P.; Soares, A. Z.; da Cunha, L. C.; Pinto, A. V.; Vargas, M. D. Bioorg. Med. Chem. 2005, 13, 193.
- (2005) Bioorg. Med. Chem , vol.13 , pp. 193
- Silva, T.M.S.¹ Camara, C.A.² Barbosa, T.P.³ Soares, A.Z.⁴ da Cunha, L.C.⁵ Pinto, A.V.⁶ Vargas, M.D.⁷

48
- 3242725162
- (d) de Moura, K. C G.; Salomão, K.; Menna-Barreto, R. F. S.; Emery, F. S.; Pinto, M. C. F. R.; Pinto, A. V.; Castro, S. L. Eur. J. Med. Chem. 2004, 39, 639.
- (2004) Eur. J. Med. Chem , vol.39 , pp. 639
- de Moura, K.C.G.¹ Salomão, K.² Menna-Barreto, R.F.S.³ Emery, F.S.⁴ Pinto, M.C.F.R.⁵ Pinto, A.V.⁶ Castro, S.L.⁷

49
- 37749053555
- General Procedure for 2H-Chromenes 7-10: A mixture of the naphthoquinone (0.02 mol, allyltriphenylphosphonium salt (0.04 mol, CHCl3 (15 mL) and aq 50% NaOH (15 mL, 0.19 mol) was vigorously stirred for 48 h at r.t. The organic phase was collected, washed with H 2O (3 x 10 mL, dried over MgSO4 and the solvent was evaporated. Purification of the crude product was achieved by flash column chromatography using hexane-CH2Cl2 as eluent. 6-Methoxy-3,3-dimethyl-3H-benzo[f]chromene (7a, IR (KBr, 2971, 2938, 1634, 1588, 1574, 1515, 1464, 1450, 1443, 1411, 1379, 1351, 1283, 1247, 1220, 1207, 1199, 1160, 1130, 1119, 1092, 996, 981, 885, 841, 755, 727, 694, 626 cm-1. 1H NMR (300 MHz, CDCl 3, δ, 1.50 (s, 6 H, Me, 3.98 (s, 3 H, OMe, 5.58 (d, J, 9.8 Hz, 1 H, H-2, 6.48 (s, 1 H, H-5, 6.95 (d, J, 9.8 Hz, 1 H, H-1, 7.30 ddd
- 3): δ = 19.0 (Me), 26.4 (Me), 30.0 (C-3), 111.0 (C-1), 112.9 (C-5), 118.3 (C-2), 125.1 (C-8a), 126.0 (C-7), 128.0 (C-6), 144.9 (C-8), 146.7 (C-4a).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.