Synthesis of 3-Substituted 2-Aminochromones via Sn(IV)-Promoted Annulation of Ynamides with 2-Methoxyaroyl Chlorides

作者: Hongxu Liu , Yanyan Yang , Shen Wang , Jie Wu , Xiao-Na Wang

DOI: 10.1021/ACS.ORGLETT.5B02137

关键词:

摘要: A Sn(IV)-promoted annulation reaction of ynamides is described for the efficient synthesis 3-substituted 2-aminochromones under mild conditions. This novel method allows a concomitant construction C–C and C–O bonds between 2-methoxyaroyl chlorides by tandem Friedel–Crafts acylation/oxo-Michael addition/elimination strategy.

参考文章(46)
C.J. Vlahos, W.F. Matter, K.Y. Hui, R.F. Brown, A specific inhibitor of phosphatidylinositol 3-kinase, 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one (LY294002). Journal of Biological Chemistry. ,vol. 269, pp. 5241- 5248 ,(1994) , 10.1016/S0021-9258(17)37680-9
R R Gorman, A H Lin, C W Benjamin, D G Wishka, J Morris, 2-Aminochromones block human platelet aggregation by inhibiting cyclic AMP-dependent phosphodiesterase leading to reduced platelet phospholipase C activity. Journal of Pharmacology and Experimental Therapeutics. ,vol. 265, pp. 457- 462 ,(1993)
Karin Dooleweerdt, Thomas Ruhland, Troels Skrydstrup, Application of ynamides in the synthesis of 2-amidoindoles. Organic Letters. ,vol. 11, pp. 221- 224 ,(2009) , 10.1021/OL802477D
Xiao-Na Wang, Hyun-Suk Yeom, Li-Chao Fang, Shuzhong He, Zhi-Xiong Ma, Brant L. Kedrowski, Richard P. Hsung, Ynamides in Ring Forming Transformations Accounts of Chemical Research. ,vol. 47, pp. 560- 578 ,(2014) , 10.1021/AR400193G
Roger J Griffin, Gabriele Fontana, Bernard T Golding, Sophie Guiard, Ian R Hardcastle, Justin JJ Leahy, Niall Martin, Caroline Richardson, Laurent Rigoreau, Martin Stockley, Graeme CM Smith, None, Selective benzopyranone and pyrimido[2,1-a]isoquinolin-4-one inhibitors of DNA-dependent protein kinase: synthesis, structure-activity studies, and radiosensitization of a human tumor cell line in vitro. Journal of Medicinal Chemistry. ,vol. 48, pp. 569- 585 ,(2005) , 10.1021/JM049526A
Søren Kramer, Karin Dooleweerdt, Anders Thyboe Lindhardt, Mario Rottländer, Troels Skrydstrup, Highly regioselective Au(I)-catalyzed hydroamination of ynamides and propiolic acid derivatives with anilines. Organic Letters. ,vol. 11, pp. 4208- 4211 ,(2009) , 10.1021/OL901565P
Wafa Gati, Mohamed M. Rammah, Mohamed B. Rammah, François Couty, Gwilherm Evano, De Novo Synthesis of 1,4-Dihydropyridines and Pyridines Journal of the American Chemical Society. ,vol. 134, pp. 9078- 9081 ,(2012) , 10.1021/JA303002A
Jian Cao, Yongping Xu, Yulong Kong, Yuming Cui, Ziqiang Hu, Guanhai Wang, Yuan Deng, Guoqiao Lai, Synthesis of δ-carbolines via a Pd-catalyzed sequential reaction from 2-iodoanilines and N-tosyl-enynamines. Organic Letters. ,vol. 14, pp. 38- 41 ,(2012) , 10.1021/OL2027762