麦克尔/环化串联反应高效合成多官能团的3,4-二氢-2H-硫吡喃[2,3-b]喹啉

Synthesis of multifunctionalized 3,4-dihydro-2H-thiopyrano[2,3-b]quinolines via a domino michael/cyclyzation reaction

为了高效合成具有喹啉并硫吡喃骨架的化合物,以新型底物2-异硫氰酸酯肉桂醛为起始原料,经过一个分子内森田-贝利斯-希尔曼反应,高收率地得到了2-巯基-3-喹啉甲醛,2-巯基-3-喹啉甲醛能与缺电子烯烃发生麦克尔/环化串联反应.结果表明,森田-贝利斯-希尔曼反应能高收率且高选择性地合成喹啉并硫吡喃衍生物.该方法具有条件温和、收率高、非对映选择性好等特点.

In order to efficiently synthesize a compound having a quinoline thiopyran structure, the novel substrate 2-isothiocyanate cinnamaldehyde was used as the starting material, and a 2-indolyl-3-quinolinaldehyde was obtained in a high yield after a molecular Morita-Bellis-Hilman reaction. 2-mercapto-3-quinolinecarboxaldehyde underwent a Michael/cyclization series reaction with an electron-deficient olefin, and a series of quinoline thiopyran derivatives was obtained with high yield and high selectivity. The method had the characteristics of mild conditions, high yield and good diastereoselectivity.