Synthesis, Table of Contents Synthesis 2021; 53(08): 1503-1512DOI: 10.1055/s-0040-1706089 paper Facile Access to 3,4-Disubstituted 2H-Chromenes via Domino [4+2] Annulation Sure Siva Prasad‡ , Dirgha Raj Joshi ‡ , Ikyon Kim ∗ Recommend Article Abstract Buy Article All articles of this category Abstract A highly efficient synthetic route to polysubstituted 2H-chromenes was developed utilizing a domino O-alkylation/intramolecular Horner–Wadsworth–Emmons (HWE) olefination of diarylmethylphosphonates, which were readily accessed via Lewis acid mediated one-pot three-component coupling of aldehydes, phenols, and triethyl phosphite. Key words Key wordschemical space - 2H-chromenes - domino reaction - intramolecular reaction - Horner–Wadsworth–Emmons olefination - one-pot three-component reaction Full Text References References 1 Pratap R, Ram VJ. Chem. Rev. 2014; 114: 10476 2a Thomas N, Zachariah SM. Asian J. Pharm. Clin. Res. 2013; 6: 11 2b Costa M, Dias TA, Brito A, Proenca F. Eur. J. Med. Chem. 2016; 123: 487 2c Xiu C, Hua Z, Xiao B. s, Tang WJ, Zhou HP, Liu XH. Expert Opin. Ther. Pat. 2017; 27: 1031 3a Lévai A, Tímár T, Sebok P, Eszenyi T. Heterocycles 2000; 53: 1193 3b Majumdar N, Paul ND, Mandal S, de Bruin B, Wulff WD. ACS Catal. 2015; 5: 2329 3c Mamaghani M, Nia RH, Tavakoli F, Jahanshahi P. Curr. Org. Chem. 2018; 22: 1704 3d Tejedor D, Delgado-Hernández S, Diana-Rivero R, Díaz-Díaz A, García-Tellado F. Molecules 2019; 24: 2904 4a El-Sepelgy O, Haseloff S, Alamsetti SK, Schneider C. Angew. Chem. Int. Ed. 2014; 53: 7923 4b Wang Z, Sun J. Synthesis 2015; 47: 3629 4c Zhao J.-J, Sun S.-B, He S.-H, Wu Q, Shi F. Angew. Chem. Int. Ed. 2015; 54: 5460 4d Jaworski AA, Scheidt KA. J. Org. Chem. 2016; 81: 10145 5a Yu J, Shi F, Gong L.-Z. Acc. Chem. Res. 2011; 44: 1156 5b de Graaff C, Ruijter E, Orru RV. A. Chem. Soc. Rev. 2012; 41: 3969 5c Multicomponent Reactions in Organic Synthesis . Zhu J, Wang Q, Wang M.-X. Wiley-VCH; Weinheim: 2015 6 Singh DK, Prasad SS, Kim J, Kim I. Org. Chem. Front. 2019; 6: 669 7 Prasad SS, Singh DK, Kim I. J. Org. Chem. 2019; 84: 6323 8 Prasad SS, Joshi DR, Lee JH, Kim I. Org. Biomol. Chem. 2020; 18: 8119 For selected examples, see: 9a Sashuk V, Peeck LH, Plenio H. Chem. Eur. J. 2010; 16: 3983 9b Hornillos V, van Zijl AW, Feringa BL. Chem. Commun. 2012; 48: 3712 9c Wang Y, Jiang M, Liu J.-T. Chem. Eur. J. 2014; 20: 15315 9d Zheng Y, Qiu L, Hong K, Dong S, Xu X. Chem. Eur. J. 2018; 24: 6705 9e Carral-Menoyo A, Misol A, Gómez-Redondo M, Sotomayor N, Lete E. J. Org. Chem. 2019; 84: 2048 10 The synthesis of 3-substituted 2H-chromenes from (2-hydroxybenzyl)triphenylphosphonium salts is a related work: Begasse B, Le Corre M. Tetrahedron 1980; 36: 3409 11 Bury PS, Christiansen LB, Jacobsen P, Jørgensen AS, Kanstrup A, Nærum L, Bain S, Fledelius C, Gissel B, Hansen BS, Korsgaard N, Thorpe SM, Wassermann K. Bioorg. Med. Chem. 2002; 10: 125 12a Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457 12b Dagar A, Seo Y, Namkung W, Kim I. Org. Biomol. Chem. 2020; 18: 3324 13 Seo Y, Choi J, Lee JH, Kim TG, Park S.-h, Han G, Namkung W, Kim I. Bioorg. Chem. 2020; 101: 104000 Supplementary Material Supplementary Material Supporting Information
