Functionalized Hexahydropyrrolo[2,1‐ b ]oxazoles from Catalyst‐Free Annulation of Δ 1 ‐Pyrrolines with Electron‐Deficient Propargylic Alcohols | Zendy

Oparina Ludmila A. | Zendy; Shabalin Dmitrii A. | Zendy; Mal'kina Anastasiya G. | Zendy; Kolyvanov Nikita A. | Zendy; Grishchenko Lyudmila A. | Zendy; Ushakov Igor' A. | Zendy; Vashchenko Alexander V. | Zendy; Trofimov Boris A. | Zendy

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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.

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