Kim Young-Shin, Park So-Young, Suh Myung-Eun, Lee Hyun-Jung, Schollmeyer Dieter
Division of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, 11-1 Daehyun-dong, Seodaemun-ku, Seoul 120-750, South Korea.
Bioorg Med Chem. 2003 Apr 17;11(8):1829-33. doi: 10.1016/s0968-0896(02)00667-3.
6,7-Dichloroquinoline-5,8-dione (1) was reacted with a number of 2-aminopyridine derivatives. Of the several possible products of this reaction, 4a,10,11-triazabenzo[3,2-a]fluorene-5,6-dione (6), produced by condensation and rearrangement, was obtained as the major product, and its structure was subsequently unambigously determined by X-ray crystallographic study. Ortho-quinones were produced via nucleophilic substitution at position C7, which was unexpected, considering that para-quinones were produced via C6 substitution in the reaction between compound 1 and ethyl acetoacetate in our previous work. Such unexpected nucleophilic substitution at C7 provides an effective, yet simple route, to the preparation of biologically active ortho-quinone derivatives.
6,7-二氯喹啉-5,8-二酮（1）与多种2-氨基吡啶衍生物发生反应。在该反应的几种可能产物中，通过缩合和重排生成的4a,10,11-三氮杂苯并[3,2-a]芴-5,6-二酮（6）是主要产物，其结构随后通过X射线晶体学研究得以明确确定。通过C7位的亲核取代生成了邻醌，这是出乎意料的，因为在我们之前的工作中，化合物1与乙酰乙酸乙酯反应时通过C6取代生成了对醌。这种在C7位意外的亲核取代为制备具有生物活性的邻醌衍生物提供了一条有效而简便的途径。
