Reactivity of sarcosine and 1,3-thiazolidine-4-carboxylic acid towards salicylaldehyde-derived alkynes and allenes
作者:Fernanda M. Ribeiro Laia、Clara S.B. Gomes、Teresa M.V.D. Pinho e Melo
DOI:10.1016/j.tet.2013.09.052
日期:2013.11
The reaction of sarcosine and 1,3-thiazolidine-4-carboxylic acid with salicylaldehyde-derived alkynes and allenes opened the way to new chromeno[4,3-b]pyrrole and chromeno[2,3-b]pyrrole derivatives. Tetrahydro-chromeno[4,3-b]pyrroles were obtained from the reaction of these secondary amino acids with O-propargylsalicylaldehyde. Interestingly, sarcosine reacted with ethyl 4-(2-formylphenoxy)but-2-ynoate
肌氨酸和1,3-噻唑烷-4-羧酸与水杨醛衍生的炔烃和丙二烯反应打开了通向新色烯并[4,3- b ]吡咯并色烯并[2,3- b ]吡咯衍生物。四氢色烯并[4,3- b从这些仲氨基酸与反应获得]吡咯ö -propargylsalicylaldehyde。有趣的是,肌氨酸用乙酸乙酯反应4-(2-甲酰基苯氧基)丁-2-炔酸甲酯,得到单环吡咯从初始形成的1,3-偶极环加成的重排得到。4-(2-甲酰基苯氧基)丁-2-炔酸甲酯与1,3-噻唑烷-4-羧酸在立体选择性方式得到预期色烯并吡咯并脱羧缩合[1,2 Ç]噻唑,其结构是由明确的X射线晶体学确定。然而,1 ħ,3 ħ吡咯并[1,2- c ^ ]距离吡喃环的开口得到的噻唑也被分离。与反应ö -丁-2,3-二烯基水杨醛,得到3-亚甲基hexahydrochromeno [4,3- b ]吡咯。ø -Allenyl水杨醛与肌氨酸和1,3-噻唑烷-4-羧酸反应