Water-Mediated Selective Synthesis of Pyrazolo[1,5-a]quinazolin-5(4H)-ones and [1,2,4]Triazolo[1,5-a]quinazolin-5(4H)-one via Copper-Catalyzed Cascade Reactions
作者： Xinying Zhang , Lin Gao , Zhangxin Wang , Xuesen Fan
DOI: 10.1080/00397911.2015.1083032
关键词:
摘要: AbstractA convenient and sustainable synthesis of pyrazolo[1,5-a]quinazolin-5(4H)-ones [1,2,4]triazolo[1,5-a]quinazolin-5(4H)-one through copper-catalyzed cascade reactions 2-bromobenzoates with 1H-pyrazol-5-amines or 1H-1,2,4-triazol-5-amine under ligand-free conditions in water is presented. It notable that aqueous medium turned out to be crucial for the chemoselective formation title compounds. Compared literature protocols, this new method showed advantages such as simple procedure, commercially available starting materials, reuse reaction together copper catalyst.
s3-eu-west-1.amazonaws.com 参考文章(9)
Sabrina Taliani, Isabella Pugliesi, Elisabetta Barresi, Silvia Salerno, Christophe Marchand, Keli Agama, Francesca Simorini, Concettina La Motta, Anna Maria Marini, Francesco Saverio Di Leva, Luciana Marinelli, Sandro Cosconati, Ettore Novellino, Yves Pommier, Roberto Di Santo, Federico Da Settimo, Phenylpyrazolo[1,5-a]quinazolin-5(4H)-one: a suitable scaffold for the development of noncamptothecin topoisomerase I (Top1) inhibitors. Journal of Medicinal Chemistry. ,vol. 56, pp. 7458- 7462 ,(2013) , 10.1021/JM400932C
Ronald Besandre, Miguel Jaimes, Jeremy A. May, Indoles Synthesized from Amines via Copper Catalysis Organic Letters. ,vol. 15, pp. 1666- 1669 ,(2013) , 10.1021/OL400444G
Xiao-Pu Fu, Li Liu, Dong Wang, Yong-Jun Chen, Chao-Jun Li, “On water”-promoted direct alkynylation of isatins catalyzed by NHC–silver complexes for the efficient synthesis of 3-hydroxy-3-ethynylindolin-2-ones Green Chemistry. ,vol. 13, pp. 549- 553 ,(2011) , 10.1039/C0GC00807A
Lin Gao, Yunping Song, Xinying Zhang, Shenghai Guo, Xuesen Fan, Copper-catalyzed tandem reactions of 2-bromobenzaldehydes/ketones with aminopyrazoles toward the synthesis of pyrazolo[1,5-a]quinazolines Tetrahedron Letters. ,vol. 55, pp. 4997- 5002 ,(2014) , 10.1016/J.TETLET.2014.07.028
Thomas E. Vasquez Jr., Thomas Nixey, Balan Chenera, Vijay Gore, Michael D. Bartberger, Yaxiong Sun, Christopher Hulme, One-pot microwave assisted preparation of pyrazoloquinazolinone libraries. Molecular Diversity. ,vol. 7, pp. 161- 164 ,(2003) , 10.1023/B:MODI.0000006917.06401.48
Yunyun Liu, Jie‐Ping Wan, Advances in Copper‐Catalyzed CC Coupling Reactions and Related Domino Reactions Based on Active Methylene Compounds Chemistry – An Asian Journal. ,vol. 7, pp. 1488- 1501 ,(2012) , 10.1002/ASIA.201101063
Veerachamy Alagarsamy, Rajani Giridhar, Mangai Ram Yadav, Synthesis and pharmacological investigation of novel 1-substituted-4-phenyl-1,2,4-triazolo[4,3-a]quinazolin-5(4H)-ones as a new class of H1-antihistaminic agents. Bioorganic & Medicinal Chemistry Letters. ,vol. 15, pp. 1877- 1880 ,(2005) , 10.1016/J.BMCL.2005.02.016
Federica Orvieto, Danila Branca, Claudia Giomini, Philip Jones, Uwe Koch, Jesus M. Ontoria, Maria Cecilia Palumbi, Michael Rowley, Carlo Toniatti, Ester Muraglia, Identification of substituted pyrazolo[1,5-a]quinazolin-5(4H)-one as potent poly(ADP-ribose)polymerase-1 (PARP-1) inhibitors. Bioorganic & Medicinal Chemistry Letters. ,vol. 19, pp. 4196- 4200 ,(2009) , 10.1016/J.BMCL.2009.05.113
Dingben Chen, Qiufang Chen, Miaochang Liu, Shuangqun Dai, Ling Huang, Jianguo Yang, Weiliang Bao, Cascade synthesis of azoquinazolinones by Cu(I)-catalyzed C–N coupling/C–H activation/C–N formation reactions under O2 Tetrahedron. ,vol. 69, pp. 6461- 6467 ,(2013) , 10.1016/J.TET.2013.05.071