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Functionalized Hexahydropyrrolo[2,1‐ b ]oxazoles from Catalyst‐Free Annulation of Δ 1 ‐Pyrrolines with Electron‐Deficient Propargylic Alcohols
Author(s) -
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.
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000582
Subject(s) - chemistry , annulation , catalysis , yield (engineering) , stereoselectivity , medicinal chemistry , combinatorial chemistry , organic chemistry , materials science , metallurgy
Electron‐deficient propargylic alcohols (EWG = CN, C(O)Ph, CO 2 Me, C(O)NH 2 ) 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.