Bibliographic Details
| Title: |
Multicomponent Domino Cyclization of Ethyl Trifluoropyruvate with Methyl Ketones and Amino Alcohols as A New Way to γ-Lactam Annulated Oxazacycles |
| Authors: |
Marina V. Goryaeva, Olesya A. Fefelova, Yanina V. Burgart, Marina A. Ezhikova, Mikhail I. Kodess, Pavel A. Slepukhin, Vasily S. Gaviko, Victor I. Saloutin |
| Source: |
Molecules, Vol 28, Iss 4, p 1983 (2023) |
| Publisher Information: |
MDPI AG, 2023. |
| Publication Year: |
2023 |
| Collection: |
LCC:Organic chemistry |
| Subject Terms: |
multicomponent domino cyclizations, ethyl trifluoropyruvate, methyl ketones, amino alcohols, γ-lactams, tetrahydropyrrolo[2,1-b]oxazolones, Organic chemistry, QD241-441 |
| More Details: |
A new route to bicyclic γ-lactams was found, which was proposed as a three-component cyclization of ethyl trifluoropyruvate with methyl ketones and 1,2-, 1,3-amino alcohols. As a result, a series of trifluoromethyl-substituted tetrahydropyrrolo [2,1-b]oxazol-5-ones and tetrahydropyrrolo[2,1-b][1,3]oxazine-6-ones was synthesized, in which the substituent at the nodal carbon atom was varied. The introduction of a twofold excess of ethyl trifluoropyruvate in reactions with amino alcohols and acetone made it possible to obtain the same bicycles, but functionalized with a hydroxyester fragment, which are formed due to four-component interactions of the reagents. Transformations with 2-butanone and aminoethanol lead predominantly to similar bicycles, while an analogous reaction with aminopropanol gives N-hydroxypropyl-2,3-dihydropyrrol-5-one. Almost all bicycles are formed as two diastereomers, the structure of which was determined using 1H, 19F, 13C NMR spectroscopy, including two-dimensional experiments and XRD analysis. A domino mechanism for the formation of tetrahydropyrrolo[2,1-b]oxazacycles was proposed, which was confirmed by their stepwise synthesis through the preliminary preparation of the aldol and bis-aldol from ethyl trifluoropyruvate and methyl ketones. |
| Document Type: |
article |
| File Description: |
electronic resource |
| Language: |
English |
| ISSN: |
1420-3049 |
| Relation: |
https://www.mdpi.com/1420-3049/28/4/1983; https://doaj.org/toc/1420-3049 |
| DOI: |
10.3390/molecules28041983 |
| Access URL: |
https://doaj.org/article/a0ae63583b9d49d69e41d372c492694f |
| Accession Number: |
edsdoj.0ae63583b9d49d69e41d372c492694f |
| Database: |
Directory of Open Access Journals |
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