Synthesis of pyridonoanthrapyrimidines

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

“…Most typically, a C−C bond is formed, although other bond types can also be obtained (e.g., C−B, Scheme 17; C−N, 43.7; N−N, 43.4; C−O, 90.2, 98.7, Schemes 96, 97; C−S, 99.2). The new ring, which may be carbo-or heterocyclic, is usually six-membered, although five- (196.4, 197.3; Charts 59, 60; Schemes 263,264,273,275,276), seven-(Schemes 13,156,157,186), and eight-membered rings (Scheme 162; 158.8, 164.3, 206.8, 268.3) have also been prepared. Nevertheless, when rings other than 6-membered are targeted, rearrangements may occur (cf., 33.3).…”

“…Related work by Tokita et al showed that, when a tertiary diamine analogous to 32.5 was subjected to cyclization in AlCl 3 –NaCl, the nonquinoidal product 32.8 was obtained (for related pyrenoid systems, see Scheme , section ). To date, the only known fully conjugated nonfused 3,9-diazaperylene is 32.10 , first reported in 1983 by Tatke and Seshadri. , However, a range of bis-lactams of the general structure 32.9 has been reported by several research groups − (for a structurally related triaza system, see ref ).…”

“… a Reagents and conditions: (a) aniline, 100 °C, 2 h; (b) acetic anhydride, AcOH, H 2 SO 4 , 20 min, reflux; (c) acetic anhydride, AcOH, H 2 SO 4 , 1 h, reflux; (d) 50% aq dioxane, 30% HCl, 20 min, reflux; (e) NHMe 2 , dioxane, 1.5 h, 20 °C; (f) heating in a capillary; (g) POCl 3 , DMF, 50 °C, 2 h; (h) NH 4 OAc, MeOH, 20 °C, 30 min. …”

“…Several triazapyrenoids were prepared by Kazankov and Bernadskii in their work on pyridonoanthrapyrimidines (Scheme 93). 156 93.1 was cyclized with aniline to form 93.2, which was in turn acetylated to yield the oxazole 93.4. The interaction of 93.4 with dimethylamine led to the amidine 93.5, which was reverted to the oxazole upon heating.…”

Heterocyclisation of trisubstituted formamidines containing an aryl or hetaryl substituent at the imine nitrogen atom

“…52 The carbonyl groups of anthraquinone can also be involved in the amidine cyclisations. 53,54 For example, 1,5-bis(3-methyl-1,3diazabut-1-enyl)-9,10-dioxo-9,10-dihydroanthracene 70 is converted into 1,3,7,9-tetraazaperylene 71 on refluxing with ammonium acetate in ethylene glycol methyl ether. 55 This reaction proved convenient for the synthesis of anthrapyrimidine dyes.…”