Synthesis of 5-azapentacene by Friedländer reaction and its properties

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• 作者：Yurngdong Jahng ; ^{ydjahng@ynu.ac.kr" class="auth_mail" title="E-mail the corresponding author} ; Moinul Karim
• 关键词：Friedlä ; nder reaction ; 3-Aminoanthracene-2-carbaldehyde ; 3-Amino-9 ; 10-dioxo-9 ; 10-dihydroanthracene-2-carbaldehyde ; 1 ; 2 ; 3 ; 4-Tetrahydronaphtho[2 ; 3-b]acridine ; 5-Azapentacene
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：7 January 2016
• 年：2016
• 卷：72
• 期：1
• 页码：199-204
• 全文大小：693 K

文摘

The Friedländer reaction of cyclohexanone with 3-aminoanthracene-2-carbaldehyde afforded corresponding 1,2,3,4-tetrahydronaphtho[2,3-b]acridine in 79%, which was also prepared by reduction of the alternative Friedländer adduct 1,2,3,4-tetrahydronaphtho[2,3-b]acridine-7,12-dione, in 56% yield. Dehydrogenation of 1,2,3,4-tetrahydronaphtho[2,3-b]acridine led to naphtha[2,3-b]acridine (5-azapentacene). 1,2,3,4-Tetrahydro-5-azapentacene and 5-azapentacene are somewhat unstable in solution while these compounds keep their identity in solid state a little longer period of time under inert gas in the refrigerator. The decomposition rate of 1,2,3,4-tetrahydro-5-azapentacene was determined by UV absorption spectra to afford a rate constant, 3.92×10⁻³ s⁻¹ (R=0.982) while 5-azapentacene was too unstable to determine the decomposition rate constant.