Department of Chemistry, Indian Institute of Technology , Kanpur 208016, India.
J Org Chem. 2016 Aug 5;81(15):6472-80. doi: 10.1021/acs.joc.6b01105. Epub 2016 Jul 28.
1,2-Naphthoquiones and their derivatives constitute an important category of compounds of relevance in pharmaceutical and material chemistry. It is shown that 1,2-naphthoquinones generated by o-iodoxybenzoic acid-mediated oxidation of 2-naphthols can be subjected to a cascade of reactions, namely oxidation, Michael addition, reduction, acetylation, and cyclocondensation, in the same pot to afford diverse 4-arylthio-1,2-naphthoquinones 2, 4-arylthio-1,2-diacetoxynaphthalenes 3, and 5-arylthio-/5-aminobenzo[a]phenazines 4 in very good isolated yields. The multistep single-pot synthesis occurs smoothly in DMF at rt.
1,2-萘醌及其衍生物是一类重要的化合物，在药物和材料化学中具有重要的应用价值。本文表明，通过邻碘酰苯甲酸介导的 2-萘酚氧化反应生成的 1,2-萘醌可以在同一个反应釜中进行一系列反应，包括氧化、迈克尔加成、还原、乙酰化和环缩合，以非常高的分离收率得到多种 4-芳基硫代-1,2-萘醌 2、4-芳基硫代-1,2-二乙酰氧基萘 3 和 5-芳基硫代-/5-氨基苯并[a]吩嗪 4。多步一锅法在室温下在 DMF 中顺利进行。
