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Chemoselectivity in the reaction of 2-diazo-3-oxo-3-phenylpropanal with aldehydes and ketones
Zhang, Jiantao,Xu, Jiaxi
, p. 1733 - 1739 (2013/10/21)
The chemoselectivity in the reaction of 2-diazo-3-oxo-3-phenylpropanal (1) with aldehydes and ketones in the presence of Et3N was investigated. The results indicate that 1 reacts with aromatic aldehydes with weak electron-donating substituents and cyclic ketones under formation of 6-phenyl-4H-1,3-dioxin-4-one derivatives. However, it reacts with aromatic aldehydes with electron-withdrawing substituents to yield 1,3-diaryl-3-hydroxypropan-1-ones, accompanied by chalcone derivatives in some cases. It did not react with linear ketones, aliphatic aldehydes, and aromatic aldehydes with strong electron-donating substituents. A mechanism for the formation of 1,3-diaryl-3-hydroxypropan-1-ones and chalcone derivatives is proposed. We also tried to react 1 with other unsaturated compounds, including various olefins and nitriles, and cumulated unsaturated compounds, such as N,N′-dialkylcarbodiimines, phenyl isocyanate, isothiocyanate, and CS2. Only with N,N′-dialkylcarbodiimines, the expected cycloaddition took place. Copyright
