Institute of Natural Sciences and Mathematics, Ural Federal University, 51 Lenina Ave., 620000 Ekaterinburg, Russia.
Molecules. 2022 Dec 16;27(24):8983. doi: 10.3390/molecules27248983.
The AgOAc-catalysed reaction of 3-nitro-2-phenyl-2-chromenes with stabilized azomethine ylides generated from the imines based on methyl glycinate and arylaldehydes leads to a mixture of and ' isomers of the corresponding chromeno[3,4-]pyrrolidines in a ratio of 2.0-2.3:1 in 85-93% total yields as a result of a Michael addition/Mannich reaction sequence. In a similar reaction involving 2-trifluoromethyl-3-nitro-2-chromenes, only chromeno[3,4-]pyrrolidines are formed in 85-94% yields. 3-Nitro-2-(trichloromethyl)-2-chromenes under the same conditions react with these azomethine ylides to give the corresponding Michael adducts as individual -isomers with the ,-configuration of the chromane ring in 40-67% yields. Some 4-CF-substituted chromano[3,4-]pyrrolidines exhibited high cytotoxic activity against HeLa human cervical carcinoma cells.
AgOAc 催化 3-硝基-2-苯基-2-色烯与基于甲甘氨酸和芳醛的稳定亚甲胺叶立德反应，生成相应的色烯并[3,4-]吡咯烷的和 '异构体混合物，产率为 85-93%，总收率为 2.0-2.3:1，这是迈克尔加成/Mannich 反应序列的结果。在涉及 2-三氟甲基-3-硝基-2-色烯的类似反应中，仅以 85-94%的产率形成 chromeno[3,4-]吡咯烷。在相同条件下，3-硝基-2-(三氯甲基)-2-色烯与这些亚甲胺叶立德反应，以 40-67%的产率得到相应的迈克尔加成产物，其为单个 -异构体，具有 chromane 环的,-构型。一些 4-CF 取代的 chromano[3,4-]吡咯烷对 HeLa 人宫颈癌细胞表现出高细胞毒性活性。
