CAJ | 학술논문

采用乙酸作溶剂和催化剂，将芳乙酮与甲醛和二级胺进行Mannich反应及热解反应，并未得到预期的Mannich碱或α，β-不饱和酮(2)，而是以较高产率(65%~73%)生成了乙酸(2-芳甲酰基)烯丙酯(3a~3o)。通过核磁共振波谱、高分辨质谱和红外光谱表征了化合物3a~3o的结构，研究了此“异常”反应的发生条件，并提出了可能的反应机理。结果表明，芳乙酮的特殊结构及反应中过量的乙酸是产生化合物3a~3o的决定因素。
채용을산작용제화최화제，장방을동여갑철화이급알진행Mannich반응급열해반응，병미득도예기적Mannich감혹α，β-불포화동(2)，이시이교고산솔(65%~73%)생성료을산(2-방갑선기)희병지(3a~3o)。통과핵자공진파보、고분변질보화홍외광보표정료화합물3a~3o적결구，연구료차“이상”반응적발생조건，병제출료가능적반응궤리。결과표명，방을동적특수결구급반응중과량적을산시산생화합물3a~3o적결정인소。
Mannich reaction is one of the most important methods for preparation ofβ-amino ketones and alde-hydes and α,β-unsaturated carbonyl compounds, as well as one of the most important basic reaction types in organic chemistry and it is widely applied as a key step in the synthesis of numerous pharmaceuticals and natu-ral products. However, during the synthesis of 1-aryl acrylic ketone 2 by the Mannich reaction of aromatic ke-tones, formaldehyde and secondary amine using acetic acid as solvent and catalyst, the Mannich base and ex-pectedα,β-unsaturated ketones 2 were not obtained and another kind of compounds 3 , 2-aryl formyl allyl ace-tate were obtained in moderate to good yields(65%-73%) . The structure of compounds 3 was confirmed by 1 H NMR, 13 C NMR, HRMS and IR spectra. The reasons of producing compounds 3 were studied and the re-sults suggested that the special structure of aromatic ketones and excess acetic acid in reaction are responsible for the exceptional Mannich reaction. In addition, the reaction mechanism was postulated.