Metal- and oxidant-free skeletal reorganizing of oxazolidines to access N-Vinylpyrroles

Multisubstituted pyrroles are important moieties in biologically active molecules and functional materials. Direct cyclization of propargylamines provides a straightforward approach to build these scaffolds; however, such a method is often hampered by the need for special reactive groups and the dif...

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Bibliographic Details
Published in:Sustainable chemistry and pharmacy 2024-12, Vol.42, p.101768, Article 101768
Main Authors: Shi, Ruidan, Xu, Xianjun, Zhong, Ling, Cao, Leilei, Pan, Ya, Huang, Junhai, Feng, Huangdi
Format: Article
Language:English
Subjects:
Cyclization
C–O activation
Metal-free
Propargylamine
Pyrrole
Ring opening
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Summary:Multisubstituted pyrroles are important moieties in biologically active molecules and functional materials. Direct cyclization of propargylamines provides a straightforward approach to build these scaffolds; however, such a method is often hampered by the need for special reactive groups and the difficulty of introducing a vinyl group on the pyrrole ring. Here we report a strategy for the skeletal reorganizing of N-propargyl oxazolidines to access N-vinylpyrroles under metal- and oxidant-free conditions. This novel reaction starts with base-mediated deprotonation/cyclization/isomerization, followed by a ring opening and β-elimination involving cleavage of two C–O bonds. The reaction, with a wide substrate range, is operationally simple and tolerates a variety of functional groups. [Display omitted] •A green skeletal editing strategy for the construction of N-vinylpyrroles from N-propargyl oxazolidines.•A highly atom- and step-economic manner under mild conditions.•A wide rang of pyrrole-derived pharmacophores to enable the development of bioactive compounds.
ISSN:2352-5541
2352-5541
DOI:10.1016/j.scp.2024.101768