Organic Reactions in Ionic Liquids: Ionic Liquid-Accelerated Cyclocondensation of α-Tosyloxyketones with 2-Aminopyridine

Yuan-Yuan  Xie; Zhen-Chu  Chen; Qin-Guo  Zheng

doi:10.1055/s-2002-33330

PAPER

Organic Reactions in Ionic Liquids: Ionic Liquid-Accelerated
Cyclocondensation of α-Tosyloxyketones with 2-Aminopyridine

Yuan-Yuan Xie^b, Zhen-Chu Chen*^a,b, Qin-Guo Zheng^c
^a Ningbo Institute of Technology, Zhejiang University, Ningbo, 315104, P. R. China
^b Department of Chemistry, Zhejiang University (Xi-Xi campus), Hangzhou, 310028, P. R. China
e-Mail: zhenchuc@mail.hz.zj.cn;
^c Pharmaceutical Sciences Research Institute, Aston University, Aston Triangle, Birmingham B4 7ET, UK

Abstract

All articles of this category

Abstract

The room temperature ionic liquid n-butylpyridinium tetrafluoroborate (BPyBF₄) is used as a ‘green’ recyclable alternative to classical molecular solvents for the cyclocondensation of α-tosyloxyketones with 2-aminopyridine. Significant rate enhancements and improved yields have been observed.

Key words

ionic liquid - 2-aminopyridine - α-tosyloxyketones - cyclocondensation

Full Text

References

1a Welton T. Chem. Rev. 1999, 99: 2071

1b Hussey CL. Pure. Appl. Chem. 1988, 60: 1763

1c Seddon KR. Kinet. Catal. 1996, 37: 693

1d Freemoutle M. Chem. Eng. News 2000, 78(15): 37

1e Wassercheid P. Keim W. Angew. Chem. Int. Ed. 2000, 39: 3772

1f Freemoutle M. Chem. Eng. News 2001, 79(1): 21

2a Surette JKD. Green L. Singer RD. Chem. Commun. 1996, 2753

2b Boon JA. Levisky JA. Pflug JL. Wilkes JS. J. Org. Chem. 1986, 51: 480

2c Adams CJ. Earle MJ. Roberts G. Seddon KR. Chem. Commun. 1998, 2097

2d Stark A. MacLean BL. Singer RD. J. Chem. Soc., Dalton Trans. 1999, 63

3 Earle MJ. McCormac PB. Seddon KR. Chem. Commun. 1998, 2245

4a Dyson PJ. Ellis DJ. Parker DG. Welton T. Chem. Commun. 1999, 25

4b Monteiro AL. Zinn FK. de Souza RF. Dupont J. Tetrahedron: Asymmetry 1997, 8: 177

4c Fisher T. Sethi A. Welton T. Woolf J. Tetrahedron Lett. 1999, 40: 793

4d Adams CJ. Earle MJ. Seddon KR. Chem. Commun. 1999, 1043

4e Einloft JEL. de Souza RF. Dupont J. Polyhedron 1996, 15: 1217

5a Howarth J. Hanlon K. Fayne D. McCormac P. Tetrahedron Lett. 1997, 38: 3097

5b Earle M. McCormac PB. Seddon RK. Green Chem. 1999, 1: 23

5c Huddleston JG. Willauer HD. Swatloski RP. Visser AE. Rogers RD. Chem. Commun. 1998, 1765

5d Song CE. Shim WH. Roh EJ. Lee S. Choi JH. Chem. Commun. 2001, 1122

6 Boulaire VL. Gree R. Chem. Commun. 2000, 2195

7a Calo V. Nacci A. Lopez L. Mannarini N. Tetrahedron Lett. 2000, 41: 8973

7b Xu LJ. Chen WP. Xiao JL. Organometallics 2000, 19: 1123

7c Carmichael AJ. Earle MJ. Holbrey JD. McCormac PB. Seddon KR. Org. Lett. 1999, 1: 997

7d Deshmukh RR. Rajagopal R. Srinivasan KV. Chem. Commun. 2001, 1544

7e Bohm VPW. Herrmann WA. Chem. Eur. J. 2000, 6: 1017

8 Calo V. Nacci A. Lopez L. Lorarro L. Tetrahedron Lett. 2000, 41: 8977

9 Mathews CJ. Smith PJ. Welton T. Chem. Commun. 2000, 1249

10 Owens GS. Omar MMA. Chem. Commun. 2000, 837

11 Dubreuil JF. Bazureau JP. Tetrahedron Lett. 2000, 41: 7351

12 Howarth J. Tetrahedron Lett. 2000, 41: 6627

13 Morrison DW. Forbes DC. James H. Tetrahedron Lett. 2001, 42: 6053

14a Zhang PF. Chen ZC. Synth. Commun. 2001, 31: 415

14b Zhang PF. Chen ZC. Synthesis 2000, 1219

14c Zhang PF. Chen ZC. Synthesis 2001, 2075

15 Dubinsky B. Shriver DA. Sanfilippo PJ. Press JB. Tobia AJ. Rosenthale ME. Drug. Dev. Res. 1990, 21: 277

16a Katsura Y. Nishino S. Inoue Y. Tomoi M. Takasugi H. Chem. Pharm. Bull. 1992, 40: 371

16b Starrett JE. Montzka TA. Crosswell AR. Cavanagh RL. J. Med. Chem. 1989, 32: 2204

17 Louis EC. inventors; US Patent 2785133. ; Chem. Abstr. 1957, 51, 9175

18 Fisher MH. Lusi A. J. Med. Chem. 1972, 15: 982

19 Tomoda H. Hirano T. Saito S. Mutai T. Araki K. Bull. Chem. Soc. Jpn. 1999, 72: 1327

20a Teulade JC. Grassy G. Escale R. Chapat JP. J. Org. Chem. 1981, 46: 1026

20b Hand ES. Paudler WW. J. Org. Chem. 1980, 45: 3738

20c Guildford AJ. Tometzki MA. Turner RW. Synthesis 1983, 987

21a Bonhôte P. Dias AP. Papageorgiou N. Kalyanasundaram K. Grätzel M. Inorg. Chem. 1996, 35: 1168

21b Suarez PAZ. Dillius JEL. Einloft S. de Souza RF. Dupont J. Polyhedron 1996, 15: 1217

22 Singh et al. reported a one-pot procedure for the preparation of imidazo[1,2-a]pyridine derivatives by cyclocondensation of ketones with [hydroxy(tosyloxy)iodo]benzene and 2-aminopyridine in acetonitrile by refluxing for 8-10 h: Singh SP. Naithani R. Prakash O. J. Indian Chem. Soc. 1998, 75: 770

23 Xie, Y. Y.; Chen, Z. C., unpublished work

24a Beilsteins Handbuch der Organischen Chemie 1st Suppl., Vol. 23: Springer Verlag; Berlin: 1936. p.62

24b Beilsteins Handbuch der Organischen Chemie 2nd Suppl., Vol. 23: Springer Verlag; Berlin: 1954. p.239

25 Balon Ya G. Shulman MD. Smirnov VA. Yukhnomenko MM. Yukhomenko MA. Zh. Org. Khim. 1990, 26: 1566 ; Chem. Abstr. 1991, 114, 81700

26 Katritzky AR. Qiu GQ. Long QH. He HY. Steel PJ. J. Org. Chem. 2000, 65: 9201

27 Artyomov VA. Shestopalov AM. Litvinov VP. Synthesis 1996, 927

28 Fisher MH. Lusi A. J. Med. Chem. 1972, 15: 982