Facile One‐pot Synthesis of Substituted Dihydropyrrol‐2‐ones via Four‐component Domino Reaction of Amines, Dialkyl Acetylenedicarboxylates and Formaldehyde
作者： Seyed Sajad Sajadikhah , Nourallah Hazeri , Malek Taher Maghsoodlou , Sayyed Mostafa Habibi-Khorassani
关键词: Formaldehyde 、 Ionic liquid 、 One-pot synthesis 、 Catalysis 、 Hydrogen Sulfate 、 Cascade reaction 、 Four component 、 Chemistry 、 Organic chemistry
摘要: A mild and efficient method for the one-pot synthesis of substituted dihydropyrrol-2-one derivatives is described via four-component domino reaction amines, dialkyl acetylenedicarboxyaltes formaldehyde in presence 1-methyl-2-oxopyrrolidinium hydrogen sulfate ([Hpyro][HSO4]) as ionic liquid catalyst. This facile approach proceeded smoothly good to high yields pure products are separated from mixture by simple filtration.
sci-hub.se 参考文章(32)
Seyed Sajad Sajadikhah, Malek Taher Maghsoodlou, Nourallah Hazeri, Sayyed Mostafa Habibi-Khorassani, Anthony C. Willis, One-pot five-component synthesis of highly functionalized piperidines using oxalic acid dihydrate as a homogenous catalyst Chinese Chemical Letters. ,vol. 23, pp. 569- 572 ,(2012) , 10.1016/J.CCLET.2012.03.008
Andrew J. Clark, Colin P. Dell, John M. McDonagh, Joanna Geden, Peter Mawdsley, Oxidative 5-Endo Cyclization of Enamides Mediated by Ceric Ammonium Nitrate Organic Letters. ,vol. 5, pp. 2063- 2066 ,(2003) , 10.1021/OL030045F
Cemalettin Alp, Deniz Ekinci, Mehmet Serdar Gültekin, Murat Şentürk, Ertan Şahin, Ömer İrfan Küfrevioğlu, A novel and one-pot synthesis of new 1-tosyl pyrrol-2-one derivatives and analysis of carbonic anhydrase inhibitory potencies. Bioorganic & Medicinal Chemistry. ,vol. 18, pp. 4468- 4474 ,(2010) , 10.1016/J.BMC.2010.04.072
Li Zhang, Yin Tan, Neng-Xue Wang, Qiong-You Wu, Zhen Xi, Guang-Fu Yang, Design, syntheses and 3D-QSAR studies of novel N-phenyl pyrrolidin-2-ones and N-phenyl-1H-pyrrol-2-ones as protoporphyrinogen oxidase inhibitors Bioorganic & Medicinal Chemistry. ,vol. 18, pp. 7948- 7956 ,(2010) , 10.1016/J.BMC.2010.09.036
Congxia Xie, Hongliang Li, Lu Li, Shitao Yu, Fusheng Liu, Synthesis of plasticizer ester using acid-functionalized ionic liquid as catalyst Journal of Hazardous Materials. ,vol. 151, pp. 847- 850 ,(2008) , 10.1016/J.JHAZMAT.2007.11.113
Qiuhua Zhu, Huanfeng Jiang, Jinghao Li, Shuwen Liu, Chenglai Xia, Min Zhang, Concise and Versatile Multicomponent Synthesis of Multisubstituted Polyfunctional Dihydropyrroles ACS Combinatorial Science. ,vol. 11, pp. 685- 696 ,(2009) , 10.1021/CC900046F
Shamila Imtiaz, Misbahul Ain Khan, Ahsan Sharif, Ejaz Ahmed, Whei-Oh Lin, Munawar Ali Munawar, Alcohols Promoted Green Protocol for Biginelli Reaction Journal of The Chinese Chemical Society. ,vol. 59, pp. 1446- 1448 ,(2012) , 10.1002/JCCS.201100472
Tummala R. K. Reddy, Chan Li, Xiaoxia Guo, Helene K. Myrvang, Peter M. Fischer, Lodewijk V. Dekker, Design, Synthesis, and Structure−Activity Relationship Exploration of 1-Substituted 4-Aroyl-3-hydroxy-5-phenyl-1H-pyrrol-2(5H)-one Analogues as Inhibitors of the Annexin A2−S100A10 Protein Interaction Journal of Medicinal Chemistry. ,vol. 54, pp. 2080- 2094 ,(2011) , 10.1021/JM101212E
Subbiah Sowmiah, Venkatesan Srinivasadesikan, Ming-Chung Tseng, Yen-Ho Chu, On the Chemical Stabilities of Ionic Liquids Molecules. ,vol. 14, pp. 3780- 3813 ,(2009) , 10.3390/MOLECULES14093780
Igor Dias-Jurberg, Fabien Gagosz, Samir Z. Zard, Unusual Approach to Branched 3-Alkynylamides and to 1,5-Dihydropyrrol-2-ones Organic Letters. ,vol. 12, pp. 416- 419 ,(2010) , 10.1021/OL902472R