1333247-79-2Relevant academic research and scientific papers
Synthesis, skeletal rearrangement, and biological activities of spirooxindoles: Exploration of a stepwise C-piancatelli rearrangement
Huang, Li,Zhang, Xiaoyu,Li, Jing,Ding, Ke,Li, Xuehui,Zheng, Wenxu,Yin, Biaolin
supporting information, p. 338 - 349 (2014/01/23)
Based on our previous studies, the scope of the transformation of 2-furylcarbinols into spirofurooxindoles, and also the skeletal rearrangements of spiro[furo-oxindoles] and spiro[thieno-oxindoles] were studied. The spiro[furo-oxindoles] thermally rearranged into spiro[pentenone-oxindoles] by a mechanism involving the conrotatory electrocyclization of the 4π-electron system. The free energy of the electrocyclization step was calculated to interpret the stereochemical outcomes. In contrast, the spiro[thieno-oxindoles] were rearranged under acidic conditions into thieno[2,3-c]quinolin-4-ones, involving an interesting dienone-phenol-like mechanism. The transformation of 2-furylcarbinols into spiro[pentenone-oxindoles] seems to be the first stepwise C-Piancatelli rearrangement. The spirooxindole products were biologically evaluated, and some of them showed promising cytotoxic activities against DU145 and LNCaP tumor cell lines. We describe the scope of the transformation of 2-furylcarbinols into spiro[furo-oxindoles], and the skeletal rearrangements of spiro[furo-oxindoles] and spiro[thieno-oxindoles]. The transformation of 2-furylcarbinols into spiro[pentenone-oxindoles] represents the first stepwise C-Piancatelli rearrangement. Some of the spirooxindole products showed promising cytotoxic activities against tumor cell lines. Copyright
A novel entry to spirofurooxindoles involving tandem dearomatization of furan ring and intramolecular friedel- Crafts reaction
Yin, Biao-Lin,Lai, Jin-Qiang,Zhang, Ze-Ren,Jiang, Huan-Feng
, p. 1961 - 1965 (2011/10/09)
A copper sulfate pentahydrate-catalyzed intramolecular Friedel-Crafts reaction using an oxocarbenium species derived from a furan ring as the alkylating agent was developed for the first time. By using this protocol, spirofurooxindoles 9 with multi-reactive sites were synthesized simply and concisely. In addition, selective hydrogenation of the endo-cyclic double bond and full hydrogenation of the endo and exo-cyclic double bonds of spirofurooxindoles 9 provided spirofurooxindoles 11 and 12, respectively. Copyright
