Quino acridine

Heald RA, Stevens MF (2003) Antitumour polycyclic acridines. Palladium(O) mediated syntheses of quino [4,3,2-kl] acridines bearing peripheral substituents as potential telomere maintenance inhibitors. Org Biomol Chem l(19) 3377-3389... 

Hutchinson 1 et al. (2004) Synthesis and properties of bioactive 2- and 3-amino-8-methyl-8H-quino[4,3,2-kl]acridine and 8,13-dimethyl-8H-quino[4,3,2-kl]acridinium salts. Org Biomol Chem 2(2) 220-228... 

Chem, 30, 881-99 (1956). Dipole moment pyridine-acids in benzene, also acids-quino-line, acridine, triethylamine. 

The synthesis of isoquino[3,4-h]acridine 40 from the interaction of p-phenylenediamine with 2-formylcyclohexanone, followed by ring closure (after in situ rearrangement) and then dehydrogenation of 39, has been reported by Berde et al. (72IJC332). Further examination of the cyclodehydration reaction also gave octahydroquino[3,2-fl]acridine 41 as the minor product, which was then dehydrogenated to provide quino[3,2-a]acridine 15 (Scheme 8) (74IJC1324). 

Among the pyridoacridine alkaloids, meridine 50 and cystodamine 51 exhibit this ring skeleton (see Section II,D,1 on pyrido[2,3,4-k/]acridines). This ring pattern can also be observed in quino[a]acridines 6 and 9 and triquinobenzene 5 (see Section II,A,1 on pyrido[2,3-a]acridines). 

Cyclocondensation of 2-aminobenzoylformic acid 98 and cyclohexane-1,2-dione dioxime 99, followed by decarboxylation with concomitant dehydrogenation of the diacid 100, gave quino[3,2-c]acridine 101 (Scheme 19) (70JPR1105). The same skeleton 102 was obtained from the Ullmann-amine coupling reaction of 2-aminobenzophenone and 1,2-diiodobenzene, followed by ring closure (85LA1501). 

Examples of the addition of solvent molecules to nitrogen-containing heterocycles, arising via initial hydrogen abstraction from the solvent, have again been described. The mechanism of this reaction with reference to six-membered aza-aromatic compounds has been the subject of a recent review,137 and in the reaction of acridine with alcohols and ethers, a radical-pair intermediate has been detected.138 Hydrogen abstraction is also implicated in the conversion of 4-quino-linecarbonitrile (172) into the alcohol (173) on irradiation in ethanol 139 the... 

A suspension of 1.0 g 9-(l,2,3-benzotriazol-l-yl)acridine in 5 mL triglyme was boiled for 4 h, and the cooled solution was diluted with excess water. The product was collected and washed with water to yield 87% 8H-quino[4,3,2-kl]acridine. 

CAS 1047-16-1 EINECS/ELINCS 213-879-2 Synonyms Cl 46500 5,12-Dihydroquino [2,3-b] acridine-7,14-dione Pigment red 122 Quinacridone Quinacridone red Quinacridone violet Quino (2,3-b) acridine-7,14-dione, 5,12-dihydro-Classification Quinacridone colorant Empirical C20H12N2O2... 

Quino-[3,2- y]acridine 12J4 5YiJ i ydione, 9CL 5,7-Dihydroquino[3,2-b]acridine-12,14-dione. lin-cis-Quinacridone [3164-44-1]... 

The isomeric linear cis-quinacridone, or isoquinacridone (6), was first described in 192h , and the linear trans-quinacridone 2, quino (3,2-b) acridine-5,12-dihydro-7, 14-dione, was synthesized by an unambiguous route by H. Liebermann and cowork-ers in Berlin in 1935. 

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