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Synthesis, Skeletal Rearrangement, and Biological Activities of Spirooxindoles: Exploration of a Stepwise C ‐Piancatelli Rearrangement
Author(s) -
Huang Li,
Zhang Xiaoyu,
Li Jing,
Ding Ke,
Li Xuehui,
Zheng Wenxu,
Yin Biaolin
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301238
Subject(s) - chemistry , du145 , stereochemistry , cope rearrangement , lncap , medicine , cancer , cancer cell
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.