One-pot synthesis of bi- and tricyclic heterocyclic compounds using benzotriazole chemistry

On the hydrolysis of diethyl 2-(perfluorophenyl)malonate

“…An exhaustive analysis of the literature revealed that virtually the same conditions were suitable for the hydrolysis of diethyl 10) [33], and diethyl 2-(4fluorophenyl)malonate (11) [6,32] (Figure 2) with minor variations in the alkali concentration and temperature. No nucleophilic substitution of activated fluorine atoms or other side reactions were observed under the conditions mentioned above.…”

“…Introduction 2-Phenylmalonic acid (1) and its esters are useful and versatile intermediates in the synthesis of many practically important compounds, e.g., pharmacologically active substances [1][2][3][4][5], in asymmetric synthesis and catalysis [6][7][8], as precursors of heterocyclic compounds [9][10][11], as ligands in coordination chemistry [12][13][14][15][16] and for other applications [17,18]. Incorporation of fluorine atoms into an organic molecule is known to be one of the most powerful tools for fine tuning of chemical and physical properties [19,20].…”

Unsymmetrically-Substituted 5,12-dihydrodibenzo[b,f][1,4]diazocine-6,11-dione Scaffold—A Useful Tool for Bioactive Molecules Design

“…In a similar way, 5,12-dihydrodibenzo[b,f ] [1,4]diazocine-6,11-dione (3a) was synthesized from benzene-1,2-diamine (4a) and dimethyl phthalate (5a). These compounds 6 [20] and 3a [13,14,18] were synthesized previously, but for the first time the crystal structures of 6 and 3a were reported by us. Surprisingly, we did not find any crystallographic structure of compounds possessing neither 1,3,4,6-tetrahydrobenzo[b] [1,4]diazocine-2,5-dione (6) nor 5,12-dihydrodibenzo[b,f ] [1,4]diazocine-6,11-dione (3) cores in the Cambridge Structural Database [21], which made this group of chemical compounds an interesting and appropriate target for crystallographic studies.…”

“…A brief literature survey revealed, that such compounds could be obtained from a condensation reaction of benzene-1,2-diamine and diethyl phthalate [13], benzene-1,2-diamine, and benzocyclobutene-l,2-dione [14,15] or Beckmann rearrangement of appropriate tricyclic dibenzoazepine oximes [16,17]. The parent compound 3 (R 1 = R 2 = R 3 = R 4 = H) could also be synthesized from benzene-1,2-diamine and 1,2-phenylenebis ((1H-benzo[d] [1,2,3]triazol-1-yl)methanone) obtained from phthaloyl dichloride and 1H-benzo [d] [1,2,3]triazole [18], while condensation of 5,6-diaminouracil with phtalic anhydride resulted in the formation of fused pyrimido [4,5-b] [1,4]diazocine ring [19].…”

Synthesis and human carbonic anhydrase I, II, VA, and XII inhibition with novel amino acid–sulphonamide conjugates

“…The syntheses of novel homosulphonamide and 4-aminoethylsulphonamide-amino acid conjugates prepared in this study are shown in Scheme 1. Since N-acylbenzotriazoles have been successfully utilised in many acylation reaction for the preparation N-, O-, S-, and C-substituted amino acid or peptides [31][32][33][34][35][36][37][38][39][40] , we chose the benzotriazole-mediated methodology to synthesise the targeted amino acid-sulphonamide conjugates. Compounds 1-12 were prepared through a facile benzotriazole mediated acylation reactions in one step (Scheme 1) at 70 C under microwave irradiation for 30 min, in dry dichloromethane as solvent, whereas compounds 13-24 were prepared using the same method except the presence of triethylamine in the reaction mixture, in order to remove hydrogen chloride from the homosulphonamide .…”