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synthesis of n-substituted acridinediones and polyhydroquinoline derivatives in refluxing water合成n - acridinediones和polyhydroquinoline衍生品在回流水.pdf

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synthesis of n-substituted acridinediones and polyhydroquinoline derivatives in refluxing water合成n - acridinediones和polyhydroquinoline衍生品在回流水

Molecules 2012, 17, 5339-5345; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Communication Synthesis of N-substituted Acridinediones and Polyhydroquinoline Derivatives in Refluxing Water Jing-Jing Xia * and Ke-Hua Zhang School of Materials and Chemical Engineering, Anhui University of Architecture, Hefei 230601, China; E-Mail: zhangkehua@ * Author to whom correspondence should be addressed; E-Mail: xiajj@; Tel.: +86-551-382-8100. Received: 13 March 2012; in revised form: 24 April 2012 / Accepted: 28 April 2012 / Published: 7 May 2012 Abstract: Acridinediones were synthesized by the one-pot Hantzsch condensation of an aromatic aldehyde, 5,5-dimethyl-1,3-cyclohexanedione, and aniline/4-methylaniline in reﬂuxing water. This method has then been extended to the four-component reaction of an aromatic aldehyde, 5,5-dimethyl-1,3-cyclohexanedione, ethyl acetoacetate and ammonium acetate for the synthesis of polyhydroquinoline derivatives. This is an environmentally friendly and efficient procedure providing good to excellent yields. Keywords: acridinedione; polyhydroquinoline; one-pot reaction; water 1. Introduction 1,4-Dihydropyridines as analogues of nicotinamide adenine dinucleotide (NADH) coenzymes exhibit a wide range of biological activities, such as calcium channel blocking, and today they are widely used in pharmacology [1]. Acridines which possess the 1,4-dihydropyridin