ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Cyclization Reactions of β,γ-Unsaturated Derivatives of Carbonic Acid. IX. Regiochemistry of Electrophilic Cyclofunctionalization of β,γ-Unsaturated Carbamic Acid Esters with Bromine - Synthesis of Oxazolidine-2-ones and Tetrahydro-2H-1,3-oxazine-2-onesN,N-Disubstituted β,γ-unsaturated urethanes (1) and bromine react in methylene chloride at room temperature. The crotyl urethanes (1a-1c and 1e) and bromine give mixtures of corresponding saturated urethanes (dibromine adducts) (2a-2c and 2e), the oxazolidine-2-ones (3a-3c and 3e), and the tetrahydro-2H-1,3-oxazine-2-ones (4a-4c and 4e). The reaction of γ,γ-dimethylallyl urethanes (1f-1h) with bromine gives similar results. A useful synthetic route to N-substituted tetrahydro-2H-1,3-oxazine-2-ones (4l-4q) is demonstrated by the reaction of cinnamyl urethanes (1l-1q) with bromine.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19863280204
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