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■ Reactions of N-Phenyl-β-aminoacohols with Acetylenic Esters

Otohiko Tsuge, Koji Oe, and Toshiyuki Ohnishi

*Research Institute of Industrial Science, Faculty of Engineering, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan

Abstract

erythro-1,2-Diphenyl-2-phenylaminoethanol 1 reacted with dimethyl acetylenedicarboxylate (DMAD) in refluxing benzene to give the cis-Michael adduct, whereas the same reaction in methanol at room temperature afforded a mixture of the Michael adduct and tetrahydro-1,4-oxazepin-7-one derivative. Although threo-isomer 4 was less reactive than 1, 4 reacted with DMAD in methanol or in the presence of triethylamine in benzene at room temperature to give the cis- or trans-Michael adduct, respectively. Photochemical and acid-catalyzed transformations of the Michael adducts to 1,4-oxazepine and oxazolidine derivatives are also described. The reaction of cis-1-hydroxy-2-phenylaminoacenaphthene 10 with DMAD gave the trans-Michael adduct, which on heating in acetic acid was converted into the corresponding oxazolidine. On the other hand, 1, 4, and 10 reacted with methyl phenylpropiolate in the presence of triethylamine in refluxing xylene afforded the corresponding oxazolidin-2-ones.