ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
2,2-Dimethyl-3-dimethylamino-2H-azirine (1) reacts with the formyl-cycloalkanones 4-8 in boiling benzene to give the 1:1 adducts 13-17 in 60-99% yield (Table). These adducts are N′-[(2-oxo-cycloalkylidene)-methyl] derivatives of 2-amino-N, N-dimethylisobutyramide. The reaction mechanism (Scheme 6) is analogous to the mechanism of the reaction of 1 with carboxylic acids and cyclic enolisable 1,3-diketones [1].Sulfinic acids and 1 undergo a similar reaction at -15° to yield 2-sulfinamido-N, N-dimethylisobutyramides (Schemes 4 and 7), while sulfonic acids and the azirine 1 lead to a dimeric salt of type 20, which with sodium hydroxide gives the dihydropyrazine 21 (Scheme 5).
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19750580423
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