Jantrapirom Jantra, Palavong Nitwaree, Tummatorn Jumreang, Thongsornkleeb Charnsak, Ruchirawat Somsak
Program on Chemical Sciences, Chulabhorn Graduate Institute, Center of Excellence on Environmental Health and Toxicology (EHT), OPS, MHESI, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand.
Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand.
Org Biomol Chem. 2023 Nov 15;21(44):8888-8901. doi: 10.1039/d3ob01492d.
Our research has led to the development of a divergent synthesis approach for the synthesis of 3,4-dihydro-2-benzo[]chromen-2-one 3 and fluorenone 9 derivatives using -alkynylarylketones as common precursors. The synthesis of 3,4-dihydro-2-benzo[]chromen-2-ones 3 employed silver catalyzed ketonization to form polycarbonyl intermediates which underwent double intramolecular cyclization and decarboxylation to generate a lactone and a phenyl ring in a one-pot fashion. In addition, the same precursor could be used to prepare fluorenone derivatives 9 under acidic conditions. The reaction proceeded the formation of indenone analogs, followed by the generation of the -quinone methide intermediate and intramolecular cyclization to provide the corresponding products in good yields.
我们的研究已开发出一种发散合成方法，以α-炔基芳基酮作为常见前体来合成3,4-二氢-2-苯并[b]色烯-2-酮3和芴酮9衍生物。3,4-二氢-2-苯并[b]色烯-2-酮3的合成采用银催化酮化反应形成多羰基中间体，该中间体经过双分子内环化和脱羧反应，以一锅法生成内酯和苯环。此外，相同的前体可用于在酸性条件下制备芴酮衍生物9。反应先形成茚酮类似物，接着生成α-醌甲基化物中间体并进行分子内环化，从而以良好的产率提供相应产物。
