Functionalized Hexahydropyrrolooxazoles from Catalyst‐Free Annulation of Δ1‐Pyrrolines with Electron‐Deficient Propargylic Alcohols

Electron‐deficient propargylic alcohols (EWG = CN, C(O)Ph, CO2Me, C(O)NH2) under catalyst‐free mild conditions are annulated with Δ1‐pyrrolines to afford functionalized hexahydropyrrolo[2,1‐b]oxazoles, mostly in 19–93 % yield. The synthesis is stereoselective with respect to disposition of functiona...

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Bibliographic Details
Published in:European journal of organic chemistry 2020-07, Vol.2020 (27), p.4181-4192
Main Authors: Oparina, Ludmila A, Shabalin, Dmitrii A, Mal'kina, Anastasiya G, Kolyvanov, Nikita A, Grishchenko, Lyudmila A, Ushakov, Igor' A, Vashchenko, Alexander V, Trofimov, Boris A
Format: Article
Language:English
Subjects:
Alcohols
Catalysts
Chemical reactions
Stereoselectivity
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Summary:Electron‐deficient propargylic alcohols (EWG = CN, C(O)Ph, CO2Me, C(O)NH2) under catalyst‐free mild conditions are annulated with Δ1‐pyrrolines to afford functionalized hexahydropyrrolo[2,1‐b]oxazoles, mostly in 19–93 % yield. The synthesis is stereoselective with respect to disposition of functionalized ethenyl group relative to the condensed heterocyclic system thus formed in most cases. This methodology provides a simple one‐pot access to a novel family of synthetically and pharmaceutically prospective.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202000582