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Tandem reaction strategy of the Passerini/Wittig reaction based on the in situ capture of isocyanides: One-pot synthesis of heterocycles
- Liu, Ming-Guo, Liu, Na, Xu, Wen-Heng, Wang, Long
- Tetrahedron 2019 v.75 no.18 pp. 2748-2754
- chemical reactions, chemical structure, off odors, organic compounds, reaction mechanisms, synthesis, toxicity
- This paper reports the tandem reaction strategy of the Passerini/Wittig reaction based on the in situ capture of isocyanides. According to this strategy, plenty of isocyanides have been synthesized, which is immediately used for the tandem reaction of Passerini/Wittig reaction in one pot. Compared to the previous work, this strategy avoids the separation, purification, and storage of isocyanides, which prominently solves the problems of isocyanide-based multicomponent reaction such as: (a) The environmentally unfriendly (strong foul odor), (a) the labile of Isocyanides, (c) high toxicity of isocyanides. In the meantime, in order to expand the application scope of our strategy, 1H-isochromenes and 3H-2-benzoxepin-1-ones have also been synthesized, which undergoes four-step transformations in one-pot. In addition, a relatively credible reaction mechanism has also been proposed, based on a series of control experiments. Furthermore, preliminary testing was performed on biological activity of some obtained compounds; These results showed that the synthesized compounds exhibited certain activity over P. digitatum and P. italicum. © 2019 Elsevier Science. All rights reserved.