On Condensation Reactions of Aceanthrene Quinone: Novel Heterocycles

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

“…For instance, fusion of the 9-oxo-1,9 a ,10-triaza-9-hydroanthracene motif to acenaphthylene yields C48.1 (Chart ), a yellow dye known from patent literature, the color of which can be tuned by substitution of the terminally fused benzene ring and other modifications. − Structurally related systems C48.2 and C48.3 were developed by Alvarez-Builla et al, , and showed enhaced binding to DNA via combination of a cationic heterocycle with a PAH moiety. Aceanthrylene systems C48.4 – 7 were reported by Amer and co-workers …”

“…Early examples include acenaphtho­[1,2- b ]­quinoxaline ( 167.2 ), prepared in 1899 by Ampola and Recchi, and a methyl derivative of aceanthra­[1,2- b ]­quinoxaline 167.4 , reported in 1911 by Liebermann and Zsuffa . Further examples were provided by Buu-Hoı̈ and Jacquignon ( C45.1 , Chart ), Klingsberg and Lewis ( C45.2 – 4 ), and Amer et al , ( C45.6 – 13 and several related 1,2,4-triazine-fused systems). Acenaphtho­[1,2- b ]­quinoxaline derivatives C45.14 – 16 were synthesized in 2014 by Nurulla et al and subjected to electrochemical polymerization. , As a result, low-bandgap polymers were obtained, which showed electrochromic switching in the NIR range.…”

Synthesis and spectroscopic properties of meso-substituted quinoxalinoporphyrins

“…This could be attributed due to the difference in the reactivity of two carbonyl groups, present in aceanthrenequinone as reported in the literature. 10 In addition, this synthetic procedure was successfully applied to obtain b,b 0 -meso-phenyl-fused quinoxalinodiporphyrins as shown in Scheme 3. For synthesizing these molecules, firstly porphyrin-a-diones (9a and 9b) were synthesized by oxidizing the 2-amino-5,10,15,20-tetraphenylporphyrin with the Dess-Martin periodinane reagent.…”

“…5- (5,10,15,quinoxalin-6-yl) -10,15,20-triphenylporphyrin (10b). Yield: 70%; found: C, 81.62; H, 4.76; N, 10.61%.…”

Single crystal X-ray structure of 3-amino-5-(4-chlorophenyl)pyridazine-4-carbonitrile

“…7 Hence, the synthesis of pyridazine derivatives has been studied for many years. [8][9][10][11][12][13][14] In continuation of recent reports on synthesis of pyridazine derivatives, [15][16][17][18][19][20][21][22][23] we would like to report the single crystal X-ray structure of 3-amino-5-(4-chlorophenyl)pyridazine-4-carbonitrile prepared by a one-pot three-component reaction of malononitrile with corresponding arylglyoxal in the presence of hydrazine hydrate at room temperature. 23 …”