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Preparation of bicyclic β-lactam and bicyclic 1,3- oxazinone scaffolds using combined cycloaddition and metathesis processes
Abstract
A simple, efficient two-step method for the preparation of heterobicyclic compounds was developed. Starting from 5-acyl or 5-carbamoyl-2,2- dimethyl-1,3-dioxa-4,5-dione bicyclic scaffolds of 1-azabicyclo[5.2.0]non- 3-en-9-one, 6,9,10,10a-tetrahydro-4H-[1,3]oxazino[3,2-a]azepin-4-one, and 6,9,10,10a-tetrahydro-2H-[1,3]oxazino[3,2-a]azepine-2,4(3H)-dione were prepared using cycloaddition of thermally generated ketenes to aldimines with unsaturated side chains, followed by metathesis. The method was applied to ring closing metathesis (RCM) of different heterocyclic substrates to demonstrate its versatility..
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- Category:
- Articles
- Type:
- artykuł w czasopiśmie wyróżnionym w JCR
- Published in:
-
SYNTHETIC COMMUNICATIONS
no. 48,
pages 1793 - 1804,
ISSN: 0039-7911 - Language:
- English
- Publication year:
- 2018
- Bibliographic description:
- Zakaszewska A., Najda-Mocarska E., Makowiec S.: Preparation of bicyclic β-lactam and bicyclic 1,3- oxazinone scaffolds using combined cycloaddition and metathesis processes// SYNTHETIC COMMUNICATIONS. -Vol. 48, nr. 14 (2018), s.1793-1804
- DOI:
- Digital Object Identifier (open in new tab) 10.1080/00397911.2018.1465980
- Verified by:
- Gdańsk University of Technology
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