期刊
TETRAHEDRON LETTERS
卷 60, 期 2, 页码 137-141出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2018.11.075
关键词
Multicomponent; Chromanone; 3,3 '-Pyrrolidinyl-spirooxindoles; Azomethine ylides; 1,3-Dipolar cycloaddition; Decarboxylation
资金
- National Natural Science Foundations of China [81660576, 81560563, 81760625]
- Project of Guizhou province [Qian Ke He Zi [2016]5623, [2015]4001, [2017]5609, Qian Jiao Yan He JG Zi [2016]06]
- Guizhou discipline construction project [GNYL[2017]008]
A new methodology was developed for the highly efficient one-pot multicomponent synthesis of chromanone-based 3,3'-pyrrolidinyl-spirooxindoles via a 1,3-dipolar cycloaddition reaction of chromones 1 with azomethine ylides (thermally generated in situ from isatins and proline or thioproline). Another valuable application of this method was for the less reactive chromone through a carboxylic acid-activation and then decarboxylation strategy, which enabled diversity-oriented synthesis of complex pirooxindoles bearing four contiguous stereocenters (one of which is a spiro quaternary stereocenter) with high efficiency and stereoselectivity (up to 90% yield and 20:1 d.r.). This protocol could provide libraries of stereochemically rich and multiple pharmecore collections, that will help in search for new drug-like molecules. (C) 2018 Elsevier Ltd. All rights reserved.
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