Synthesis, Table of Contents Synthesis 2024; 56(12): 1932-1940DOI: 10.1055/a-2241-2196 paper Iron-Catalyzed [2+1+2+1] Annulation of Amines and N,N-Dimethyl Enaminones using N,N-Dimethylaminoethanol as a One-Carbon Synthon for the Synthesis of 1,4-Dihydropyridines Wanqian Ma , Qiulin Kuang , Suzhen Li , Mengyi Guo , Yibo Song , Luoteng Cheng , Jianyong Yuan∗ Recommend Article Abstract Buy Article All articles of this category Abstract A simple and efficient method for the synthesis of 1,4-dihydropyridines from amines, N,N-dimethyl enaminone and N,N-dimethylaminoethanol in a four-component [2+1+2+1] annulation catalyzed by FeCl3 has been established, where N,N-dimethylaminoethanol was applied as a methine source. The procedure was executed smoothly, resulting in the synthesis of a wide range of 1,4-dihydropyridines with moderate to good yields. Additionally, these fluorophores exhibited good photophysical characteristics. Key words Key words1,4-dihydropyridines - N,N-dimethylaminoethanol - annulation - multi-component reactions - iron catalysis Full Text References References 1a Edraki N, Mehdipour AR, Khoshneviszadeh M, Miri R. Drug Discovery Today 2009; 14: 1058 1b Yu F.-C, Zhou B, Xu H, Chang K.-J, Shen Y. Tetrahedron Lett. 2015; 56: 837 1c Parthiban A, Makam P. RSC Adv. 2022; 12: 29253 1d Mathur R, Negi KS, Shrivastava R, Nair R. RSC Adv. 2021; 11: 1376 2 Abbas H.-AS, El Sayed WA, Fathy NM. Eur. J. Med. Chem. 2010; 45: 973 3 Triggle DJ. Cell. Mol. Neurobiol. 2003; 23: 293 4 De Luca M, Ioele G, Ragno G. Pharmaceutics 2019; 11: 85 5 Briede J, Stivrina M, Vigante B, Stoldere D, Duburs G. Cell Biochem. Funct. 2008; 26: 238 6 Refat HM, Fadda AA. Eur. J. Med. Chem. 2013; 70: 419 7 Sun C, Chen Y, Liu T, Wu Y, Fang T, Wang J, Xing J. Chin. J. Chem. 2012; 30: 1415 8 Zheng C, You S.-L. Chem. Soc. Rev. 2012; 41: 2498 9 Chen W, Liu Z, Tian J, Li J, Ma J, Cheng X, Li G. J. Am. Chem. Soc. 2016; 138: 12312 10 Hantzsch A. Justus Liebigs Ann. Chem. 1882; 215: 1 11 Debache A, Ghalem W, Boulcina R, Belfaitah A, Rhouati S, Carboni B. Tetrahedron Lett. 2009; 50: 5248 12 Wan J.-P, Gan S.-F, Sun G.-L, Pan Y.-J. J. Org. Chem. 2009; 74: 2862 13 Wan J, Zhou Y, Liu Y, Fang Z, Wen C. Chin. J. Chem. 2014; 32: 219 14 Li S, Yang Q, Wang J. Tetrahedron Lett. 2016; 57: 4500 15 Zhao Y, Guo X, Ding X, Zhou Z, Li M, Feng N, Gao B, Lu X, Liu Y, You J. Org. Lett. 2020; 22: 8326 16a Cao S, Zhong S, Hu C, Wan J.-P, Wen C. Chin. J. Chem. 2015; 33: 568 16b Girling PR, Batsanov AS, Shen HC, Whiting A. Chem. Commun. 2012; 48: 4893 16c Wang L.-M, Sheng J, Zhang L, Han J.-W, Fan Z.-Y, Tian H, Qian C.-T. Tetrahedron 2005; 61: 1539 16d Yang J, Wang C, Xie X, Li H, Li Y. Eur. J. Org. Chem. 2010; 4189 16e Song S, Wang Y, Yu F. Top. Curr. Chem. 2023; 381: 30 17a Geng M, Huang M, Kuang J, Fang W, Miao M, Ma Y. J. Org. Chem. 2022; 87: 14753 17b Qin Z, Ma R, Ying S, Li F, Ma Y. Adv. Synth. Catal. 2022; 364: 3263 17c Qin Z, Zhang R, Ying S, Ma Y. Org. Chem. Front. 2022; 9: 5624 18a Lu Y.-N, Ma C, Lan J.-P, Zhu C, Mao Y.-J, Mei G.-J, Zhang S, Shi F. Org. Chem. Front. 2018; 5: 2657 18b Bhattacherjee D, Ram S, Chauhan AS, Yamini, Sheetal, Das P. Chem. Eur. J. 2019; 25: 5934 18c Duan Y.-G, Hu X.-M, Cao X.-L, Lv K.-H, Yan S.-J. Org. Lett. 2021; 23: 6866 18d Guo H, Liu Y, Wen C, Wan J.-P. Green Chem. 2022; 24: 5058 18e Sheng H, Chen Z, Li X, Su J, Song Q. Org. Chem. Front. 2022; 9: 3000 18f Tao S, Xu L, Yang K, Zhang J, Du Y. Org. Lett. 2022; 24: 4187 18g Zhou Y, Wang L.-S, Lei S.-G, Gao Y.-X, Ma J.-T, Yu Z.-C, Wu Y.-D, Wu A.-X. Org. Chem. Front. 2022; 9: 4416 19a Dalai PG, Panda N. Adv. Synth. Catal. 2022; 364: 3736 19b Ma J.-T, Wang L.-S, Chai Z, Chen X.-F, Tang B.-C, Chen X.-L, He C, Wu Y.-D, Wu A.-X. Chem. Commun. 2021; 57: 5414 19c Su M.-D, Liu H.-P, Cao Z.-Z, Liu Y, Li H, Nie Z.-W, Yang T.-L, Luo W.-P, Liu Q, Guo C.-C. J. Org. Chem. 2021; 86: 13446 19d Wang A, Liu X, Kong Y, Wang J, Jiang T.-S. Org. Chem. Front. 2021; 8: 947 20 Sun Y, Chai Z, Liu D, Zhang M, Chen L, Liu Z, Wang Y, Yu F. Chem. Eur. J. 2023; 29: e202300297 21a Barrios-Bermúdez N, González-Avendaño M, Lado-Touriño I, Cerpa-Naranjo A, Rojas-Cervantes M. Nanomaterials 2020; 10: 749 21b Jiao L, Xu Z, Du W, Li H, Yin M. ACS Appl. Mater. Interfaces 2017; 9: 28339 21c Ma B, Wang S, Liu F, Zhang S, Duan J, Li Z, Kong Y, Sang Y, Liu H, Bu W, Li L. J. Am. Chem. Soc. 2019; 141: 849 21d Mirzaei A, Chen Z, Haghighat F, Yerushalmi L. Chemosphere 2017; 174: 665 22 Wang F, Sun W, Wang Y, Jiang Y, Loh T.-P. Org. Lett. 2018; 20: 1256 23 Kim J, Hong SH. Chem. Sci. 2017; 8: 2401 24 Zhao Y, Wang H, Kang X, Zhang R, Feng N, Su Q. Org. Chem. Front. 2022; 9: 5935 Supplementary Material Supplementary Material Supporting Information
