Mishra Gitanjali, Sasmal Mukesh, Chakraborty Arundhuti, Thirupathi Barla
Department of Chemical Sciences, Indian Institute of Science Education and Research Berhampur, Transit Campus, Govt. ITI Building, NH 59, Engineering School Road, Ganjam-District, 760 010, Berhampur, Odisha, India.
Chemistry. 2023 Dec 19;29(71):e202301976. doi: 10.1002/chem.202301976. Epub 2023 Nov 13.
Synthesis of highly functionalized spiro[4.4]nonane and spiro[4.5]decane motifs by the reaction of dimethylacetylenedicarboxylate (DMAD) with 2-(2'-ketoalkyl)-1,3-indandiones and 2-(3'-ketoalkyl)-1,3-indandiones, respectively, has been developed by utilizing a catalytic amount of DABCO. The tertiary hydroxy-containing spiro[4.4]nonane products were converted into fully conjugated pentafulvene π-systems in an acidic medium through dehydration and unprecedented C-C bond rearrangement.
通过使用催化量的1,4 - 二氮杂双环[2.2.2]辛烷（DABCO），分别使二甲基乙炔二羧酸酯（DMAD）与2 - （2'- 氧代烷基）-1,3 - 茚二酮和2 - （3'- 氧代烷基）-1,3 - 茚二酮反应，开发了高官能化螺[4.4]壬烷和螺[4.5]癸烷结构单元的合成方法。含叔羟基的螺[4.4]壬烷产物在酸性介质中通过脱水和前所未有的C - C键重排转化为完全共轭的戊搭烯π体系。
