Xanthan sulfuric acid as an efficient catalyst
495
13. Casiraghi G, Zanardi F, Rassu G, Pinna L (1996) Org Prep Proced
Int 28:641
14. Hantzsch A (1890) Ber Dtsch Chem Ges 23:1474
15. Ferreira VF, De Souza MCBV, Cunha AC, Pereira LOR, Ferreira
MLG (2002) Org Prep Proced Int 33:411
16. Kleinspehn GG (1955) J Am Chem Soc 77:1546
17. Hamby JM, Hodges JC (1993) Heterocycles 35:843
18. Alberola A, Ortega AG, Sadaba ML, Sanudo C (1999) Tetrahe-
dron 55:6555
19. Elghamry I (2002) Synth Commun 32:897
20. Jones RA, Been GP (1977) The chemistry of pyrroles, chapter 3.
Academic, New York
CHCl3, 1.00 g chlorosulfonic acid (9 mmol) was added
dropwise at 0 °C during 2 h. After addition was complete,
the mixture was stirred for 2 h until HCl was removed from
the reaction vessel. The mixture was then filtered and
washed with 30 cm3 methanol or acetonitrile and dried at
room temperature to afford 5.26 g xanthan sulfuric acid as
white powder. The number of H? sites on the xanthan-
OSO3H was determined by acid–base titration to be
0.58 meq/g.
21. Chiu PK, Sammes MP (1990) Tetrahedron 46:3439
22. Sreekumar R, Padmakumar R (1998) Synth Commun 28:1661
23. Yu SX, Le Quesne PW (1995) Tetrahedron Lett 36:6205
24. Texier-Boullet F, Klein B, Hamelin J (1986) Synthesis 409
25. Kidwai K, Singhal K, Rastogi S (2006) J Heterocycl Chem
43:1231
26. Raghavan S, Anuradha K (2003) Synlett 711
27. Zhu XH, Chen G, Xu ZL (2008) Chin Youji Hauaxue 28:115
28. Drewes SE, Hogan CJ (1989) Synth Commun 19:2101
29. Banik BK, Samajdar S, Banik I (2004) J Org Chem 69:213
30. Shaw DJ, Wood WF (1992) J Chem Edu 69:A313
31. Samajdar S, Becker FF, Banik BK (2001) Heterocycles 55:1019
General experimental procedure for the preparation
of N-substituted pyrroles
To a mixture of amine 1 (1 mmol) and 2,5-hexanedione
(2a, 1 mmol) was added 0.10 g XSA. The mixture was
stirred at room temperature for the appropriate time
according to Table 2. The progress of the reaction was
monitored by TLC (eluent: n-hexane/ethyl acetate 3:1).
After completion of the reaction, 10 cm3 EtOAc was
added. The mixture was filtered, and the xanthan sulfuric
acid was washed with 10 cm3 EtOAc. The filtrate was
evaporated and the residue was purified by column chro-
matography and by recrystallization to afford the pure
product.
¨ ¨
32. Abid M, Spaeth A, Torok B (2006) Adv Synth Catal 348:2191
33. Jin Zheng C, Zhang XX, Su WK (2006) Tetrahedron Lett
47:5383
34. Banik BK, Banik I, Renteria M, Dasgupta SK (2004) Tetrahedron
Lett 45:3417
35. De K, Surya K (2008) Catal Lett 124:174
36. Chen JX, Liu MC, Yang XL, Ding JC, Wu HY (2008) J Braz
Chem Soc 19:34
37. Armugam P, Perumal PT (2006) Chem Lett 35:632
38. Curini M, Montanari F, Rosati O, Lioy E, Margarita R (2003)
Tetrahedron Lett 44:3923
All pyrrole products are known compounds and were
characterized by IR and NMR spectroscopy data and their
melting points, which agreed with reported values.
Acknowledgments The author is grateful to NISOC for providing
xanthan and RIPI for performing the elemental analysis.
39. Veisi H (2010) Tetrahedron Lett 51:2109
40. Luo H, Kang Y, Li Q, Yang L (2008) Heteroatom Chem 19:144
41. Wang B, Gu Y, Luo C, Yang T, Yang L, Suo J (2004) Tetra-
hedron Lett 45:5873
42. Rao HSP, Jothilingam S, Scheeren HW (2004) Tetrahedron
60:1625
References
43. Zhang ZH, Li JJ, Li TS (2008) Ultrason Sonochem 15:673
44. Danks TN (1999) Tetrahedron Lett 40:3975
45. Sargent EV, Adolph J, Clemmons MK, Kirk GD, Pena BM,
Fedoruk MJ (1990) J Occup Med 32:625
46. Davidson RL (ed) (1980) Handbook of water-soluble gums and
resins. McGraw-Hill, New York
47. Whistler RL, BeMiller JN (eds) (1973) Industrial gums: poly-
saccharides and their derivatives. Academic Press, New York,
London
48. Breslow R (1980) Acc Chem Res 13:170
49. Clark JH, Macquarrie DJ (2002) Green chemistry and technol-
ogy. Blackwell, Abingdon
1. Raimondi MV, Cascioferro S, Schillaci D, Petruso S (2006) Eur J
Med Chem 41:1439
2. Rochais C, Lisowski V, Dallemagne P, Rault S (2006) Biorg Med
Chem 14:8162
3. Lee D, Swager TM (2003) J Am Chem Soc 125:6870
4. Cooney JV, Mcewen WE (1981) J Org Chem 46:2570
5. Higgins SJ (1997) Chem Soc Rev 26:247
6. Lee C-F, Yang L-M, Hwu T-Y, Feng A-S, Tseng J-C, Luh T-Y
(2000) J Am Chem Soc 122:4992
7. Nizurski-Mann RE, Cava MP (1992) Heterocycles 34:2003
8. Chou SSP, Yeh YH (2001) Tetrahedron Lett 42:1309
9. Batista RMF, Costa SPG, Malheiro EL, Belsley M, Raposo
MMM (2007) Tetrahedron 63:4258
50. Shaabani A, Maleki A, Soudi MR, Mofakham H (2009) Catal
Commun 10:945
51. Rahmatpour A (2002) J Chem Res (S) 2:118
52. Rahmatpour A (2010) J Heterocycl Chem 47:1011
53. Rahmatpour A, Banihashemi A (1999) Tetrahedron 55:7271
54. Rahmatpour A (2010) React Funct Polym 70:923
55. He Y-H, Wang G-Q, Guan Z (2010) J Heterocycl Chem 47:486
10. Raposo MMM, Sousa MRC, Kirsch G, Cardoso P, Belsley M,
Gomes EM, Fonseca AMC (2006) Org Lett 8:3681
11. Silva CD, Walker DA (1998) J Org Chem 63:6715
12. De Lacy Costello BPJ, Guemion N, Ratcliffe NM, Sivanand PS,
Teare GC (2000) Synth Met 114:181
123