Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2002(11): 1505-1508
DOI: 10.1055/s-2002-33330
DOI: 10.1055/s-2002-33330
PAPER
© Georg Thieme Verlag Stuttgart · New York
Organic Reactions in Ionic Liquids:
Ionic Liquid-Accelerated
Cyclocondensation of α-Tosyloxyketones
with 2-Aminopyridine
Further Information
Received
6 February 2002
Publication Date:
23 August 2002 (online)
Publication History
Publication Date:
23 August 2002 (online)
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
-
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