1,3,7-Triazapyrenes: the unexpected products of the reaction of 1,8-diaminonaphthalene with 1,3,5-triazines in polyphosphoric acid

A Greener Approach Synthesis and Docking Studies of Perimidine Derivatives as Potential Anticancer Agents

“…The mechanistic pathways are described by the formation of the intermediates (6) and (9), which undergoes in situ elimination of water or alcohol molecule to yield the products (7a-f) and (10a-f), respectively, as single product (Scheme 2). The structure of the obtained products (7a-f) and (10a-f) was confirmed on the bases of their elemental analyses and spectral data (FT-IR, 1 H-NMR, 19 F-NMR, 13 C-NMR, and LC-MS/MS). Thus, the analytical data for (7b) revealed a molecular formula C 28 H 20 FN 5 O. LC-MS (ionization method): m/z 462 [M +1].…”

“…1 H-NMR (400 MHz, DMSO-d 6 ) spectrum of compound (7b) showed a two singlet at δ = 12.44 and 10.83 ppm assigned for the 2NH groups. 19 F-NMR (400 MHz, DMSO-d 6 ) gave multiplet signal at δ = À108.49 because of the presence of fluorine atom, whereas 13 C-NMR (400 MHz, DMSO-d 6 ) showed the appearance of signal corresponding to the (perimidin C-2) at δ = 155.3 ppm. This procedure afforded product yields of up to 90% in short time (Table 2).…”

“…In addition to their biological activity including antiulcer, antimicrobial, and antifungal properties , more recently, the DNA binding affinity and antitumor potential of many perimidine derivatives have been investigated . Perimidine derivatives proved to be valuable starting substances for the preparation of more complex polyheterocycles . Traditionally, synthesis of perimidine derivatives was achieved using conventional solvent‐based synthetic routes with low to moderate yields .…”

Formylation and acetylation of 2-ethoxynaphthalene with 1,3,5-triazines in polyphosphoric acid

“…2 In the present work, we report on the reaction of 2 ethoxynaphthalene (1) with 1,3,5 triazines 2a,b in PPA. * We showed that monoformylation (acety lation) of compound 1 in this system proceeds already at room temperature and comes to a completion at 40-45 °C in case of triazine 2a and at 55-60 °C in case of 2b for 2 h. The yields of the products of monoacylation 3a and 3b under these conditions were 81 and 85%, respec tively.…”

Synthesis of bipyridyls by the reaction of allylpyridines with 1,3,5-triazine in polyphosphoric acid

“…Recently, we have shown that 1,3,5 tri azines in polyphosphoric acid (PPA) are efficient reagents for the peri annulation of the pyridine ring to azaphen alenes 2,3 and 1,8 naphthylenediamine. 4 We assumed that this system can be used for the synthesis of substituted pyridines. In the present work, we report on the reaction of 1,3,5 triazines 1a,b with allylpyridines 2a,b in PPA.…”