SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 4, 2009, Pages 569-572

H2O2/Fe(NO3)3-promoted synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles

(3) Bahrami, Kiumars a Khodaei, Mohammad Mehdi a Naali, Fardin a

a RAZI UNIVERSITY (Iran)

Author keywords

2 arylbenzimidazole; 2 arylbenzothiazole; Aryl aldehydes; Chemoselectivity; Hydrogen peroxide; Solvent free

Indexed keywords

EID: 62249124735 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087911 Document Type: Article

Times cited : (73)

References (45)

1
- 12444297980
- Navarrete-Vázquez, G.; Yepez-Mulia, L.; Hernández-Campos, A.; Tapia, A.; Hernández-Luis, F.; Cedillo, R.; González, J.; Martínez-Fernández, M.; Martínez-Grueiro, M.; Castillo, R. Bioorg. Med. Chem. 2003, 11, 4615.
- (2003) Bioorg. Med. Chem , vol.11 , pp. 4615
- Navarrete-Vázquez, G.¹ Yepez-Mulia, L.² Hernández-Campos, A.³ Tapia, A.⁴ Hernández-Luis, F.⁵ Cedillo, R.⁶ González, J.⁷ Martínez-Fernández, M.⁸ Martínez-Grueiro, M.⁹ Castillo, R.¹⁰

2
- 13444301272
- (a) Özden, S.; Atabey, D.; Yildiz, S.; Göker, H. Bioorg. Med. Chem. 2005, 13, 1587.
- (2005) Bioorg. Med. Chem , vol.13 , pp. 1587
- Özden, S.¹ Atabey, D.² Yildiz, S.³ Göker, H.⁴

3
- 0015024221
- (b) Palmer, P. J.; Trigg, R. B.; Warrington, J. V. J. Med. Chem. 1971, 14, 248.
- (1971) J. Med. Chem , vol.14 , pp. 248
- Palmer, P.J.¹ Trigg, R.B.² Warrington, J.V.³

4
- 0036952881
- (a) Andrzejewska, M.; Yépez-Mulia, L.; Cedillo-Rivera, R.; Tapia, A.; Vilpo, L.; Vilpo, J.; Kazimierczuk, Z. Eur. J. Med. Chem. 2002, 37, 973.
- (2002) Eur. J. Med. Chem , vol.37 , pp. 973
- Andrzejewska, M.¹ Yépez-Mulia, L.² Cedillo-Rivera, R.³ Tapia, A.⁴ Vilpo, L.⁵ Vilpo, J.⁶ Kazimierczuk, Z.⁷

5
- 0032903677
- (b) Hall, I. H.; Peaty, N. J.; Henry, J. R.; Easmon, J.; Heinisch, G.; Purstinger, G. Arch. Pharm. (Weinheim, Ger.) 1999, 332, 115.
- (1999) Arch. Pharm. (Weinheim, Ger.) , vol.332 , pp. 115
- Hall, I.H.¹ Peaty, N.J.² Henry, J.R.³ Easmon, J.⁴ Heinisch, G.⁵ Purstinger, G.⁶

6
- 0038067133
- Bénéteau, V.; Besson, T.; Guillard, J.; Léonce, S.; Pfeiffer, B. Eur. J. Med. Chem. 1999, 34, 1053.
- (1999) Eur. J. Med. Chem , vol.34 , pp. 1053
- Bénéteau, V.¹ Besson, T.² Guillard, J.³ Léonce, S.⁴ Pfeiffer, B.⁵

7
- 0038630972
- Kücükbay H., Durmaz R., Orhan E., Günal S.; Farmaco; 2003, 58: 431.
- (2003) Farmaco , vol.58 , pp. 431
- Kücükbay, H.¹ Durmaz, R.² Orhan, E.³ Günal, S.⁴

8
- 0029081625
- (a) Benazzouz, A.; Boraud, T.; Dubédat, P.; Boireau, A.; Stutzmann, J.-M.; Gross, C. Eur. J. Pharmacol. 1995, 284, 299.
- (1995) Eur. J. Pharmacol , vol.284 , pp. 299
- Benazzouz, A.¹ Boraud, T.² Dubédat, P.³ Boireau, A.⁴ Stutzmann, J.-M.⁵ Gross, C.⁶

9
- 0033614947
- (b) Jimonet, P.; Audiau, F.; Barreau, M.; Blanchard, J.-C.; Boireau, A.; Bour, Y.; Coléno, M.-A.; Doble, A.; Doerflinger, G.; Huu, C. D.; Donat, M.-H.; Duchesne, J. M.; Ganil, P.; Guérémy, C.; Honoré, E.; Just, B.; Kerphirique, R.; Gontier, S.; Hubert, P.; Laduron, P. M.; Blevec, J. L.; Meunier, M.; Miquet, J.-M.; Nemecek, C.; Pasquet, M.; Piot, O.; Pratt, J.; Rataud, J.; Reibaud, M.; Stutzmann, J.-M.; Mignani, S. J. Med. Chem. 1999, 42, 2828.
- (1999) J. Med. Chem , vol.42 , pp. 2828
- Jimonet, P.¹ Audiau, F.² Barreau, M.³ Blanchard, J.-C.⁴ Boireau, A.⁵ Bour, Y.⁶ Coléno, M.-A.⁷ Doble, A.⁸ Doerflinger, G.⁹ Huu, C.D.¹⁰ Donat, M.-H.¹¹ Duchesne, J.M.¹² Ganil, P.¹³ Guérémy, C.¹⁴ Honoré, E.¹⁵ Just, B.¹⁶ Kerphirique, R.¹⁷ Gontier, S.¹⁸ Hubert, P.¹⁹ Laduron, P.M.²⁰ more..

10
- 0033552891
- (a) Hamdouchi, C.; de Blas, J.; del Prado, M.; Gruber, J.; Heinz, B. A.; Vance, L. J. Med. Chem. 1999, 42, 50.
- (1999) J. Med. Chem , vol.42 , pp. 50
- Hamdouchi, C.¹ de Blas, J.² del Prado, M.³ Gruber, J.⁴ Heinz, B.A.⁵ Vance, L.⁶

11
- 0033612293
- (b) Girardet, J.-L.; Townsend, L. B. J. Org. Chem. 1999, 64, 4169.
- (1999) J. Org. Chem , vol.64 , pp. 4169
- Girardet, J.-L.¹ Townsend, L.B.²

12
- 0034218354
- (c) Yeh, C.-M.; Tung, C.-L.; Sun, C.-M. J. Comb. Chem. 2000, 2, 341.
- (2000) J. Comb. Chem , vol.2 , pp. 341
- Yeh, C.-M.¹ Tung, C.-L.² Sun, C.-M.³

13
- 0033937315
- (d) Chen, J. J.; Wei, Y.; Drach, J. C.; Townsend, L. B. J. Med. Chem. 2000, 43, 2449.
- (2000) J. Med. Chem , vol.43 , pp. 2449
- Chen, J.J.¹ Wei, Y.² Drach, J.C.³ Townsend, L.B.⁴

14
- 0035843328
- (e) Tumelty, D.; Cao, K.; Holmes, C. P. Org. Lett. 2001, 3, 83.
- (2001) Org. Lett , vol.3 , pp. 83
- Tumelty, D.¹ Cao, K.² Holmes, C.P.³

15
- 0035905830
- (f) Mann, J.; Baron, A.; Opoku-Boahen, Y.; Johansson, E.; Parkinson, G.; Kelland, L. R.; Neidle, S. J. Med. Chem. 2001, 44, 138.
- (2001) J. Med. Chem , vol.44 , pp. 138
- Mann, J.¹ Baron, A.² Opoku-Boahen, Y.³ Johansson, E.⁴ Parkinson, G.⁵ Kelland, L.R.⁶ Neidle, S.⁷

16
- 0039486054
- (g) Raju, B.; Nguyen, N.; Holland, G. W. J. Comb. Chem. 2002, 4, 320.
- (2002) J. Comb. Chem , vol.4 , pp. 320
- Raju, B.¹ Nguyen, N.² Holland, G.W.³

17
- 0038897328
- (h) Akamatsu, H.; Fukase, K.; Kusumoto, S. J. Comb. Chem. 2002, 4, 475.
- (2002) J. Comb. Chem , vol.4 , pp. 475
- Akamatsu, H.¹ Fukase, K.² Kusumoto, S.³

18
- 0038700561
- (i) Hoesl, C. E.; Nefzi, A.; Houghten, R. A. J. Comb. Chem. 2003, 5, 155.
- (2003) J. Comb. Chem , vol.5 , pp. 155
- Hoesl, C.E.¹ Nefzi, A.² Houghten, R.A.³

19
- 0037474661
- (j) Vourloumis, D.; Takahashi, M.; Simonsen, K. B.; Ayida, B. K.; Barluenga, S.; Winters, G. C.; Hermann, T. Tetrahedron Lett. 2003, 44, 2807.
- (2003) Tetrahedron Lett , vol.44 , pp. 2807
- Vourloumis, D.¹ Takahashi, M.² Simonsen, K.B.³ Ayida, B.K.⁴ Barluenga, S.⁵ Winters, G.C.⁶ Hermann, T.⁷

20
- 0032971926
- (a) Chua, M.-S.; Shi, D.-F.; Wrigley, S.; Bradshaw, T. D.; Hutchinson, I.; Shaw, P. N.; Barrett, D. A.; Stanley, L. A.; Stevens, M. F. G. J. Med. Chem. 1999, 42, 381.
- (1999) J. Med. Chem , vol.42 , pp. 381
- Chua, M.-S.¹ Shi, D.-F.² Wrigley, S.³ Bradshaw, T.D.⁴ Hutchinson, I.⁵ Shaw, P.N.⁶ Barrett, D.A.⁷ Stanley, L.A.⁸ Stevens, M.F.G.⁹

21
- 0033533836
- (b) Kashiyama, E.; Hutchinson, I.; Chua, M.-S.; Stinson, S. F.; Phillips, L. R.; Kaur, G.; Sausville, E. A.; Bradshaw, T. D.; Westwell, A. D.; Stevens, M. F. G. J. Med. Chem. 1999, 42, 4172.
- (1999) J. Med. Chem , vol.42 , pp. 4172
- Kashiyama, E.¹ Hutchinson, I.² Chua, M.-S.³ Stinson, S.F.⁴ Phillips, L.R.⁵ Kaur, G.⁶ Sausville, E.A.⁷ Bradshaw, T.D.⁸ Westwell, A.D.⁹ Stevens, M.F.G.¹⁰

22
- 0035953321
- (c) Hutchinson, I.; Chua, M.-S.; Browne, H. L.; Trapani, V.; Bradshaw, T. D.; Westwell, A. D.; Stevens, M. F. G. J. Med. Chem. 2001, 44, 1446.
- (2001) J. Med. Chem , vol.44 , pp. 1446
- Hutchinson, I.¹ Chua, M.-S.² Browne, H.L.³ Trapani, V.⁴ Bradshaw, T.D.⁵ Westwell, A.D.⁶ Stevens, M.F.G.⁷

23
- 0035800309
- (d) Leng, W.; Zhou, Y.; Xu, Q.; Liu, J. Macromolecules 2001, 34, 4774.
- (2001) Macromolecules , vol.34 , pp. 4774
- Leng, W.¹ Zhou, Y.² Xu, Q.³ Liu, J.⁴

24
- 0037203997
- (e) Hutchinson, I.; Jennings, S. A.; Vishnuvajjala, B. R.; Westwell, A. D.; Stevens, M. F. G. J. Med. Chem. 2002, 45, 744.
- (2002) J. Med. Chem , vol.45 , pp. 744
- Hutchinson, I.¹ Jennings, S.A.² Vishnuvajjala, B.R.³ Westwell, A.D.⁴ Stevens, M.F.G.⁵

25
- 34247604973
- Blackwell: Oxford
- Kochi, M. Green Reaction Media for Organic Synthesis; Blackwell: Oxford, 2005.
- (2005) Green Reaction Media for Organic Synthesis
- Kochi, M.¹

26
- 0042709821
- Seddon, K. R. Nature (London) 2003, 2, 363.
- (2003) Nature (London) , vol.2 , pp. 363
- Seddon, K.R.¹

27
- 0003908350
- Strukul, G, Ed, Kluwer Academic: Dordrecht
- Catalytic Oxidations with Hydrogen Peroxide as Oxidant; Strukul, G., Ed.; Kluwer Academic: Dordrecht, 1992.
- (1992) Catalytic Oxidations with Hydrogen Peroxide as Oxidant

28
- 0043198185
- Noyori, R.; Aoki, M.; Sato, K. Chem. Commun. 2003, 1977.
- (2003) Chem. Commun , pp. 1977
- Noyori, R.¹ Aoki, M.² Sato, K.³

29
- 32644457240
- (a) Bahrami, K. Tetrahedron Lett. 2006, 47, 2009.
- (2006) Tetrahedron Lett , vol.47 , pp. 2009
- Bahrami, K.¹

30
- 34247885886
- (b) Khodaei, M. M.; Bahrami, K.; Khedri, M. Can. J. Chem. 2007, 58, 7.
- (2007) Can. J. Chem , vol.58 , pp. 7
- Khodaei, M.M.¹ Bahrami, K.² Khedri, M.³

31
- 45249119955
- (c) Khodaei, M. M.; Bahrami, K.; Karimi, A. Synthesis 2008, 1682.
- (2008) Synthesis , pp. 1682
- Khodaei, M.M.¹ Bahrami, K.² Karimi, A.³

32
- 49149091529
- (d) Bahrami, K.; Khodaei, M. M.; Kamali, S. Chin. J. Chem. 2008, 26, 1119.
- (2008) Chin. J. Chem , vol.26 , pp. 1119
- Bahrami, K.¹ Khodaei, M.M.² Kamali, S.³

33
- 33947541193
- Bahrami, K.; Khodaei, M. M.; Kavianinia, I. Synthesis 2007, 547.
- (2007) Synthesis , pp. 547
- Bahrami, K.¹ Khodaei, M.M.² Kavianinia, I.³

34
- 0029061671
- Eynde, J. J. V.; Delfosse, F.; Lor, P.; Haverbeke, Y. V. Tetrahedron 1995, 51, 5813.
- (1995) Tetrahedron , vol.51 , pp. 5813
- Eynde, J.J.V.¹ Delfosse, F.² Lor, P.³ Haverbeke, Y.V.⁴

35
- 33751396188
- Das, B.; Holla, H.; Srinivas, Y. Tetrahedron Lett. 2007, 48, 61.
- (2007) Tetrahedron Lett , vol.48 , pp. 61
- Das, B.¹ Holla, H.² Srinivas, Y.³

36
- 33744825729
- Wang, Y.; Sarris, K.; Sauer, D. R.; Djuric, S. W. Tetrahedron Lett. 2006, 47, 4823.
- (2006) Tetrahedron Lett , vol.47 , pp. 4823
- Wang, Y.¹ Sarris, K.² Sauer, D.R.³ Djuric, S.W.⁴

37
- 0037631073
- Ben-Alloum, A.; Bougrin, K.; Soufiaoui, M. Tetrahedron Lett. 2003, 44, 5935.
- (2003) Tetrahedron Lett , vol.44 , pp. 5935
- Ben-Alloum, A.¹ Bougrin, K.² Soufiaoui, M.³

38
- 28544451672
- Gogoi, P.; Konwar, D. Tetrahedron Lett. 2006, 47, 79.
- (2006) Tetrahedron Lett , vol.47 , pp. 79
- Gogoi, P.¹ Konwar, D.²

39
- 0032543469
- Ben-Alloum, A.; Bakkas, S.; Souflaoui, M. Tetrahedron Lett. 1998, 39, 4481.
- (1998) Tetrahedron Lett , vol.39 , pp. 4481
- Ben-Alloum, A.¹ Bakkas, S.² Souflaoui, M.³

40
- 0032500083
- Bougrin, K.; Loupy, A.; Souflaoui, M. Tetrahedron 1998, 54, 8055.
- (1998) Tetrahedron , vol.54 , pp. 8055
- Bougrin, K.¹ Loupy, A.² Souflaoui, M.³

41
- 0001560434
- Hein, D. W.; Alheim, R. J.; Leavitt, J. J. J. Am. Chem. Soc. 1957, 79, 427.
- (1957) J. Am. Chem. Soc , vol.79 , pp. 427
- Hein, D.W.¹ Alheim, R.J.² Leavitt, J.J.³

42
- 0030862001
- Ben-Alloum, A.; Bakkas, S.; Souflaoui, M. Tetrahedron Lett. 1997, 38, 6395.
- (1997) Tetrahedron Lett , vol.38 , pp. 6395
- Ben-Alloum, A.¹ Bakkas, S.² Souflaoui, M.³

43
- 62249104644
- Ferric nitrate, hydrogen peroxide (30, as well as all the aromatic aldehydes, 1,2-phenylenediamine derivatives and 2-aminothiophenol employed as substrates are commercially available and were used without further purification. The concentration of the commercial 30% H2O2 solution was checked iodometrically prior to use. General procedure for the Synthesis of Benzimidazoles and Benzothiazoles: A mixture of 1,2-phenylenediamine (1 mmol, aryl aldehyde (1 mmol, H2O 2 (30, 4 mmol, 0.4 mL) and Fe(NO3)3·9 H2O (0.1 mmol, 0.04 g) was heated at 50°C for the appropriate time as mentioned in Table 2. After completion of the reaction, the reaction mixture was dissolved in EtOH (10 mL) and then poured into ice-water (30 mL, The pure solid product was filtered, washed with ice-water and subsequently dried. An identical procedure was employed using 2-aminothiophenol (1 mmol, aryl aldehyde (1 mmol) in t
- 6): δ = 22.0, 122.0, 123.5, 125.5, 126.7, 127.9, 130.2, 131.3, 135.4, 141.9, 154.6, 168.7.

44
- 0242326253
- Charlton, P. T.; Mlalipliant, G. K.; Oxley, P.; Peak, D. A. J. Chem. Soc. 1951, 485.
- (1951) J. Chem. Soc , pp. 485
- Charlton, P.T.¹ Mlalipliant, G.K.² Oxley, P.³ Peak, D.A.⁴

45
- 0000691918
- George, B.; Papadopoulos, E. P. J. Org. Chem. 1977, 42, 441.
- (1977) J. Org. Chem , vol.42 , pp. 441
- George, B.¹ Papadopoulos, E.P.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.