1,1,3,3-N,N,N′,N′-Tetramethylguanidinium trifluoroacetate as an ionic liquid, efficiently promotes one-pot, three-component condensation of aldehydes, alkyl nitriles and α-hydroxy or α-amino activated C–H acid to afford the corresponding pyran annulated heterocyclic systems. Ionic liquid can be recycled for subsequent reactions without any appreciable loss of efficiency.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
G.R. Green J.M. Evans A.K. Vong (1995) NoChapterTitle A.R. Katritzky C.W. Ress E.F.V. Scriven (Eds) Comprehensive Heterocyclic Chemistry II NumberInSeriesVol. 5 Pergamon Press Oxford 469
C. Wienter C.H. Schroeder B.D. West K.J.P. Link (1962) J. Org. Chem. 27 3086
T. Kuwada K. Harada J. Nobuhiro T. Choshi (2002) Heterocycles 57 2081
P. Srivastava, A.S. Saxena and V.J. Ram, Synthesis (2000) 541
A.D. Broom J.L. Shim G.L. Anderson (1976) J. Org. Chem. 41 1095 Occurrence Handle10.1021/jo00869a003 Occurrence Handle1255289
H.C. Scarborough (1964) J. Org. Chem. 29 219
J.L. Shim R. Niess A.D. Broom (1972) J. Org. Chem. 37 578 Occurrence Handle10.1021/jo00969a013 Occurrence Handle5061435
B.H. Rizkalla A.D. Broom (1972) J. Org. Chem. 37 3980 Occurrence Handle10.1021/jo00798a002 Occurrence Handle4643014
F. Schönfeld R. Troschütz (2001) Heterocycles 55 1679
E.C. Taylor K. Lee (1997) Heterocycles 45 2229
E.V. Stoyanov I.C. Ivanov D. Heber (2000) Molecules 5 19
V.K. Ahluwalia R. Kumar A. Khurana R. Bhatla (1990) Tetrahedron 46 3953 Occurrence Handle10.1016/S0040-4020(01)90530-7
E.M.A. Yakout, N.M. Ibrahim, K.M. Ghoneim and M.R.H. Mahran, J. Chem. Res. (S) (1999) 652
V. Nair A.U. Vinod R. Ramesh R.S. Menon L. Varma S. Mathew A. Chiaroni (2002) Heterocycles 58 147
I. Yavari and M.T. Maghsoodlou, J. Chem. Res. (S) (1998) 386
I. Devi B.S.D. Kumar P.J. Bhuyan (2003) Tetrahedron Lett. 44 8307 Occurrence Handle10.1016/j.tetlet.2003.09.063
A. Shaabani M.B. Teimouri S. Arab-Ameri (2004) Tetrahedron Lett. 45 8409 Occurrence Handle10.1016/j.tetlet.2004.09.039
A. Shaabani M.B. Teimouri H.R. Bijanzadeh (2004) Monatsh. Chem. 135 589
A. Shaabani M.B. Teimouri H.R. Bijanzadeh (2004) Monatsh. Chem. 135 441
(a) T. Welton, Chem. Rev. 99 (1999) 2071; (b) P. Wasserscheid and W. Keim, Angew. Chem. Int. Ed. 39 (2000) 3772; (c) R. Sheldon, Chem. Commun. (2001) 2399
X.S. Wang D.Q. Shi S.J. Tu C.S. Yao (2003) Synth. Commun. 33 119 Occurrence Handle10.1081/SCC-120015567
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Shaabani, A., Samadi, S., Badri, Z. et al. Ionic Liquid Promoted Efficient and Rapid One-pot Synthesis of Pyran Annulated Heterocyclic Systems. Catal Lett 104, 39–43 (2005). https://doi.org/10.1007/s10562-005-7433-2
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s10562-005-7433-2