Base-catalyzed one-pot synthesis of dispiro-1,3-dioxolane bisoxindoles from N-methylisatin and methyl propiolate

作者: Su Yeon Kim , Hwa Jung Roh , Da Young Seo , Ji Yeon Ryu , Junseong Lee

DOI: 10.1016/J.TETLET.2017.01.055

关键词: DiastereomerOne-pot synthesisCascade reactionMedicinal chemistryChemistryDioxolaneOxyanionIsatinReaction mechanismAcetylideStereochemistry

摘要: Abstract Base-catalyzed domino reaction between N-methylisatin and methyl propiolate afforded four diastereomeric dispiro-1,3-dioxolane bisoxindoles. The mechanism involved sequential 1,2-addition of acetylide anion to the carbonyl group isatin, resulting oxyanion a second molecule final 5-exo-dig cyclization process.

参考文章(88)
Basi V. Subba Reddy, Govindaraju Karthik, Tamilselvan Rajasekaran, Balasubramanian Sridhar, Stereoselective Synthesis of Highly Functionalized Dispirooxindoles through [3+2] Cycloaddition of Carbonyl Ylides with 3-Arylideneoxindoles European Journal of Organic Chemistry. ,vol. 2015, pp. 2038- 2041 ,(2015) , 10.1002/EJOC.201500002
Yan-Hua Sun, Yu Xiong, Chu-Qin Peng, Wu Li, Jun-An Xiao, Hua Yang, Highly stereoselective construction of novel dispirooxindole-imidazolidines via self-1,3-dipolar cyclization of ketimines. Organic and Biomolecular Chemistry. ,vol. 13, pp. 7907- 7910 ,(2015) , 10.1039/C5OB00954E
Rong Zhou, Kai Zhang, Yusong Chen, Qiang Meng, Yiyi Liu, Ruifeng Li, Zhengjie He, P(NMe2)3-mediated reductive [1+4] annulation of isatins with enones: a facile synthesis of spirooxindole-dihydrofurans Chemical Communications. ,vol. 51, pp. 14663- 14666 ,(2015) , 10.1039/C5CC03676C
Qi-Lin Wang, Tian Cai, Jing Zhou, Fang Tian, Xiao-Ying Xu, Li-Xin Wang, An unprecedented base-promoted domino reaction of methyleneindolinones and N-tosyloxycarbamates for the construction of bispirooxindoles and spiroaziridine oxindoles Chemical Communications. ,vol. 51, pp. 10726- 10729 ,(2015) , 10.1039/C5CC03793J
David Tejedor, Fernando García-Tellado, José Juan Marrero-Tellado, Pedro de Armas, Efficient domino process based on the catalytic generation of non-metalated, conjugated acetylides in the presence of aldehydes or activated ketones. Chemistry: A European Journal. ,vol. 9, pp. 3122- 3131 ,(2003) , 10.1002/CHEM.200204579
Yun-Lin Liu, Xin Wang, Yu-Lei Zhao, Feng Zhu, Xing-Ping Zeng, Long Chen, Cui-Hong Wang, Xiao-Li Zhao, Jian Zhou, One‐Pot Tandem Approach to Spirocyclic Oxindoles Featuring Adjacent Spiro‐Stereocenters Angewandte Chemie. ,vol. 52, pp. 13735- 13739 ,(2013) , 10.1002/ANIE.201307250
Maria M.M. Santos, Recent advances in the synthesis of biologically active spirooxindoles Tetrahedron. ,vol. 70, pp. 9735- 9757 ,(2014) , 10.1016/J.TET.2014.08.005
Hao Wu, Li-Li Zhang, Zhi-Qing Tian, Yao-Dong Huang, Yong-Mei Wang, Highly Efficient Enantioselective Construction of Bispirooxindoles Containing Three Stereocenters through an Organocatalytic Cascade Michael–Cyclization Reaction Chemistry: A European Journal. ,vol. 19, pp. 1747- 1753 ,(2013) , 10.1002/CHEM.201203221
David Tejedor, Sara López-Tosco, Gabriela Méndez-Abt, Fernando García-Tellado, Fluoride‐Triggered Domino Reactions Involving Ammonium Acetylides and Carbonyl Compounds European Journal of Organic Chemistry. ,vol. 2010, pp. 33- 37 ,(2010) , 10.1002/EJOC.200901082