Abstract
But-2-ynedioic acid diethyl ester reacted with an amine and an aldehyde to afford polysubstituted ethyl 2,5-dihydro-2H -1,3-oxazine-6-one-4-carboxylate derivatives in good to excellent yields.
Key words
three-component synthesis - but-2-ynedioic acid diethyl ester - amines - aldehydes - dihydro-2H -1,3-oxazine-6-ones
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Experimental Procedure: To a stirring mixture of but-2-ynedioic acid diethyl ester (1 , 170 mg, 1 mmol) and aniline (2a , 93 mg, 1 mmol), benzaldehyde (3a , 127 mg, 1.2 mmol), solvent mixture (3 mL, MeCN-H2 O, 10:1) and KOH (1.2 mmol, 67 mg) were added successively. The mixture was stirred at r.t. for 30 min. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with Et2 O and dried with anhyd MgSO4 . Then, the mixture was filtered and washed with Et2 O (5 × 5 mL). The combined organic solvent was evaporated in vacuo and the crude product was purified by preparative TLC with hexane-EtOAc (10:1) as the eluent to afford the desired product 4aa (252 mg, 78%) as a yellowish solid.
