Abstract
An efficient and green approach for the synthesis of 7H-thiazolo[3,2-b][1,2,4]triazin-7-one derivatives is described via one-pot, three-component condensation of arylpyruvic acids, thiosemicarbazide, and 2-bromoacetophenones in the presence of N-methylpyrrolidone hydrosulfate ([Hnmp]HSO4) ionic liquid as the catalyst and solvent. This green catalyst can be recycled several times without any substantial decrease in the yields and reaction rates. The catalyst loadings are high.
Graphical abstract
Similar content being viewed by others
References
van der Geer J, Hanraads JAJ, Lupton RA (2000) J Sci Commun 163:51
Zulfiqar F, Kitazume T (2000) Green Chem 2:296
Lin YL, Cheng JY, Chu YH (2007) Tetrahedron 63:10849
Peng JJ, Deng YQ (2001) Tetrahedron Lett 42:5917
Fang D, Luo J, Zhou XL, Ye ZW, Liu ZL (2007) J Mol Catal A Chem 274:208
Harjani JR, Nara SJ, Salunkhe MM (2002) Tetrahedron Lett 43:1127
Yue CB, Mao AQ, Wei YY (2008) Catal Commun 9:1571
Potdar MK, Mohile SS, Salunkhe MM (2001) Tetrahedron Lett 42:9285
Lee JK, Kim DC, Song CE, Lee S (2003) Synth Commun 33:2301
Fischer T, Sethi A, Welton T, Woolf J (1999) Tetrahedron Lett 40:793
Xiao Y, Malhotra SV (2004) Tetrahedron Lett 45:8339
Song CE, Shim WH, Roh EJ, Choi JH (2000) Chem Commun 17:1695
Xiao Y, Malhotra SV (2005) J Mol Catal A Chem 230:129
Lee S, Park JH (2002) Bull Korean Chem Soc 23:1367
Liu SJ, Yang L, Jin Z, Huang EF (2009) Arkivoc X:333
Liu SJ, Yang L, Liu XG, Luo Y (2010) Lett Drug Des Discov 7:5
Jin Z, Yang L, Liu SJ, Wang J (2010) Arch Pharm Res 33:1641
Jin Z, Liu XG, Liu SJ, Gao HY (2011) Chin J Med Chem 20:25
Liu SJ, Yang L, Liu XG, Jin Z, Wan DC, Lin HQ, Hu C (2009) Chin J Med Chem 19:251
Acknowledgments
We are grateful to Prof. Hu for discussions and Mr. Hao ChE for measuring the MS and NMR spectra.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Liu, S., Shi, L., He, J. et al. A green method for synthesis of 7H-thiazolo[3,2-b][1,2,4]triazin-7-one derivatives catalyzed by N-methylpyrrolidone hydrosulfate ([Hnmp]HSO4) ionic liquid. Monatsh Chem 145, 217–221 (2014). https://doi.org/10.1007/s00706-013-1009-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-013-1009-4