NaH promoted [4+3] annulation of crotonate-derived sulfur ylides with thioaurones: synthesis of 2,5-dihydrobenzo[4,5]thieno[3,2-b]oxepines

作者: Youquan Zhang , Aimin Yu , Jiru Jia , Shanshan Ma , Ke Li

DOI: 10.1039/C7CC04466F

关键词:

摘要: The [4+3] annulation reaction of crotonate-derived sulfur ylides with thioaurones has, for the first time, been reported using NaH as base. A diverse array 2,5-dihydrobenzo[4,5]thieno[3,2-b]oxepines is obtained in good to excellent yields. proposed mechanism investigated and supported by DFT calculations.

参考文章(36)
Yufen Liu, Yanlong Du, Aimin Yu, Dabin Qin, Xiangtai Meng, Diverse synthesis of pyrano[2,3-b]indol and dihydropyrano[2,3-b]indol via tunable Lewis bases catalyzed domino reactions Tetrahedron. ,vol. 71, pp. 7706- 7716 ,(2015) , 10.1016/J.TET.2015.07.057
Muhammad Yar, Sven P. Fritz, Paul J. Gates, Eoghan M. McGarrigle, Varinder K. Aggarwal, Synthesis of N-Vinyloxazolidinones and Morpholines from Amino Alcohols and Vinylsulfonium Salts: Analysis of the Outcome's Dependence on the N-Protecting Group by Nanospray Mass Spectrometry European Journal of Organic Chemistry. ,vol. 2012, pp. 160- 166 ,(2012) , 10.1002/EJOC.201101272
Yufen Liu, Qi Zhang, Yanlong Du, Aimin Yu, Kui Zhang, Xiangtai Meng, Convenient synthesis of substituted tetrahydrofuran via Lewis base catalyzed [3 + 2] domino reactions RSC Advances. ,vol. 4, pp. 52629- 52632 ,(2014) , 10.1039/C4RA09249J
Artur Nenov, Thorben Cordes, Teja T. Herzog, Wolfgang Zinth, Regina de Vivie-Riedle, Molecular Driving Forces for Z/E Isomerization Mediated by Heteroatoms: The Example Hemithioindigo Journal of Physical Chemistry A. ,vol. 114, pp. 13016- 13030 ,(2010) , 10.1021/JP107899G
Song Ye, Zheng-Zheng Huang, Chun-An Xia, Yong Tang, Li-Xin Dai, A novel chiral sulfonium yilde: highly enantioselective synthesis of vinylcyclopropanes. Journal of the American Chemical Society. ,vol. 124, pp. 2432- 2433 ,(2002) , 10.1021/JA0172969
Javier Izquierdo, Ane Orue, Karl A. Scheidt, A Dual Lewis Base Activation Strategy for Enantioselective Carbene-Catalyzed Annulations Journal of the American Chemical Society. ,vol. 135, pp. 10634- 10637 ,(2013) , 10.1021/JA405833M
J. Plötner, A. Dreuw, Molecular mechanism of the Z/E-photoisomerization of hemithioindigo hemistilbene. Journal of Physical Chemistry A. ,vol. 113, pp. 11882- 11887 ,(2009) , 10.1021/JP903156J
Aleksandr V. Marenich, Christopher J. Cramer, Donald G. Truhlar, Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. Journal of Physical Chemistry B. ,vol. 113, pp. 6378- 6396 ,(2009) , 10.1021/JP810292N