Novel isocyanide-based three-component reaction: a facile synthesis of substituted 1H-chromeno[2,3-d]pyrimidine-5-carboxamides
作者： Ebrahim Soleimani , Somayeh Ghorbani , Hamid Reza Ghasempour
DOI: 10.1016/J.TET.2013.06.080
关键词:
摘要: Abstract A mild and efficient method for the synthesis of 1 H -chromeno[2,3- d ]pyrimidine-5-carboxamide derivatives via a one-pot, three-component reaction an isocyanide, barbituric acid, salicylaldehyde in presence acetic acid ethanol/water mixture at 75 °C is reported. This high atom economy led to construction one benzopyran ring, amide group single synthetic step.
elsevier.com
sci-hub.se 参考文章(37)
Alexander Dömling, Recent advances in isocyanide-based multicomponent chemistry Current Opinion in Chemical Biology. ,vol. 6, pp. 306- 313 ,(2002) , 10.1016/S1367-5931(02)00328-9
Ahmad Shaabani, Ebrahim Soleimani, Hamid Reza Khavasi, Synthesis of 1-aminoimidazo[5,1-a]isoquinolinium salts based on multicomponent reactions of isocyanides. ACS Combinatorial Science. ,vol. 10, pp. 442- 446 ,(2008) , 10.1021/CC700196H
José Daniel Figueroa-Villar, Elizabete R. Cruz, A simple approach towards the synthesis of oxadeazaflavines Tetrahedron. ,vol. 49, pp. 2855- 2862 ,(1993) , 10.1016/S0040-4020(01)80384-7
Masahiro Murakami, New Catalyzed Three‐Component Cycloadditions for the Synthesis of Eight‐Membered Carbocycles Angewandte Chemie. ,vol. 42, pp. 718- 720 ,(2003) , 10.1002/ANIE.200390200
Qiong Chen, Xiao-Lei Zhu, Li-Li Jiang, Zu-Ming Liu, Guang-Fu Yang, Synthesis, antifungal activity and CoMFA analysis of novel 1,2,4-triazolo[1,5-a]pyrimidine derivatives European Journal of Medicinal Chemistry. ,vol. 43, pp. 595- 603 ,(2008) , 10.1016/J.EJMECH.2007.04.021
Anu Agarwal, Ramesh, Ashutosh, Neena Goyal, Prem M.S. Chauhan, Suman Gupta, Dihydropyrido[2,3-d]pyrimidines as a new class of antileishmanial agents. Bioorganic & Medicinal Chemistry. ,vol. 13, pp. 6678- 6684 ,(2005) , 10.1016/J.BMC.2005.07.043
Ebrahim Soleimani, Mohsen Zainali, Isocyanide-based multicomponent reactions: synthesis of alkyl-2-(1-(alkylcarbamoyl)-2,2-dicyanoethyl)benzoate and isochromeno[3,4-b]pyrrole derivatives. Journal of Organic Chemistry. ,vol. 76, pp. 10306- 10311 ,(2011) , 10.1021/JO201908F
Chen-Yu Cheng, Hsin-I Chiu, Ming-Jyh Chang, Yen-Chung Lin, Ming-Cheng Tsai, Hon-Cheng Yu, Synthesis of 2,3,4a,11b-tetrahydro-oxazino[2,3-c]benzopyran-9-carbonitriles as ATP-sensitive potassium channel openers Bioorganic & Medicinal Chemistry Letters. ,vol. 8, pp. 463- 468 ,(1998) , 10.1016/S0960-894X(98)00046-8
Hugues Bienaymé, Chris Hulme, Gilles Oddon, Philippe Schmitt, Maximizing Synthetic Efficiency: Multi-Component Transformations Lead the Way Chemistry - A European Journal. ,vol. 6, pp. 3321- 3329 ,(2000) , 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO;2-A
Ronghui Lin, Sigmond G. Johnson, Peter J. Connolly, Steven K. Wetter, Eva Binnun, Terry V. Hughes, William V. Murray, Niranjan B. Pandey, Sandra J. Moreno-Mazza, Mary Adams, Angel R. Fuentes-Pesquera, Steven A. Middleton, Synthesis and evaluation of 2,7-diamino-thiazolo[4,5-d] pyrimidine analogues as anti-tumor epidermal growth factor receptor (EGFR) tyrosine kinase inhibitors Bioorganic & Medicinal Chemistry Letters. ,vol. 19, pp. 2333- 2337 ,(2009) , 10.1016/J.BMCL.2009.02.067