ISSN:
0170-2041
Keywords:
6H-1,2-Oxazines
;
γ-Lactams
;
Lewis acids
;
Ring contraction
;
Phosphite, trimethyl
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Unexpected Formation of γ-Lactams from 6H-1,2-Oxazines Promoted by Lewis AcidsThe reaction of 6H-1,2-oxazine 1 with trimethylsilyl cyanide in the presence of titanium tetrachloride provides α,β-unsaturated γ-lactam 3. Similarly, Lewis acid-promoted addition of trimethyl phosphite towards 1 affords a mixture of γ-lactams 8 and 9. The structure of 9 was established by X-ray analysis. A plausible mechanism for the formation of these γ-lactams by Lewis acid-induced ring contraction is proposed.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1992199201106
