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Abstract：
Quinolone and quinoline derivatives are frequently found as substructures in pharmaceutically active compounds. In this paper, we describe a procedure for the synthesis of azuleno[2,1-b]quinolones and quinolines from 2-arylaminoazulene derivatives, which are readily prepared via the aromatic nucleophilic substitution reaction of a 2-chloroazulene derivative with several arylamines. The synthesis of azuleno[2,1-b]quinolones was established by the Brønsted acid-catalyzed intramolecular cyclization of 2-arylaminoazulene derivatives bearing two ester groups at the five-membered ring. The halogenative aromatization of azuleno[2,1-b]quinolones with POCl3 yielded azuleno[2,1-b]quinolines with a chlorine substituent at the pyridine moiety. The aromatic nucleophilic substitution reaction of azuleno[2,1-b]quinolines bearing chlorine substituent with secondary amines was also investigated to afford the aminoquinoline derivatives. These synthetic methodologies reported in this paper should be valuable in the development of new pharmaceuticals based on the azulene skeleton.
摘要：
喹诺酮和喹啉衍生物经常被发现作为药物活性化合物中的亚结构。在本文中,我们描述了从2-芳基氨基偶氮ulene衍生物合成偶氮并[2,1-b]喹诺酮和喹啉的方法，它们很容易通过2-氯代独烯衍生物与几种芳基胺的芳族亲核取代反应制备。Azuleno[2,1-b]喹诺酮的合成是通过布朗斯台德酸催化的2-芳基氨基azulene衍生物的分子内环化反应建立的，该衍生物在五元环上带有两个酯基。用POCl3对偶氮并[2,1-b]喹诺酮进行卤化芳构化，得到在吡啶部分带有氯取代基的偶氮并[2,1-b]喹啉。还研究了带有氯取代基的azuleno[2,1-b]喹啉与仲胺的芳族亲核取代反应，以提供氨基喹啉衍生物。本文报道的这些合成方法在开发基于青霉烯骨架的新药物方面应该是有价值的。
