Synthesis of functionally substituted 2-oxa-6-azabicyclo[2.2.2]octanes based on Schiff bases and secondary arylamides of acetoacetic acid
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Recently we have shown, that aminocyclohexenone derivatives 2 are formed by the reaction of N-alkylimines 1 with acetylacetone (R3 = Me) or acetoacetic ester (R3 = EtO)  at room temperature in ethanol. These compounds are also formed from enamines of mentioned dicarbonyl compounds . In the present work, we have studied the reactions of Schiff bases 1a-d with secondary amides of acetoacetic acid 3a,b. By the analogous reaction, the compounds containing simultaneously aminocyclohexene and amide groups might be obtained which may be of interest from the pharmacological point of view. However on the basis of IR and 1H NMR spectroscopy, it was established that 8-aryl-N,6-bis(aryl)-3-hydroxy-1,3-dimethyl-5-oxo-2-oxa-6-aza-bicyclo[2.2.2]octane-7-carboxyamides 4a-c are formed in these reactions in 30-60% yields.
Presumably, the reaction proceeds via addition of arylamides 3a,b to imines 1a-d with subsequent elimination of a primary amine R2NH2 and the formation of the chalkone 5. The...
Keywordsamide imine lactam hemiketal
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