Abstract
Herein, we report a facile synthesis of ethyl-2-(4-aminophenoxy)acetate 4 as a building synthon for novel dual hypoglycemic agents. This building template was synthesized by alkylation of 4-nitrophenol with ethyl bromo-acetate followed by selective reduction of the nitro group. This reduction methoddoes not require nascent hydrogen or any reaction complexity; it goes easily via consecutive reaction in NH4Cl/Fe to yield our target synthon as very pure crystals. This product was characterized by (HNMR)-H-1, (CNMR)-C-13, COSY, NOESY NMR spectroscopy, and elemental analysis. Additionally, its structure was studied and approved by X-ray single crystal structure determination. The unit cell parameters are a = 8.2104(6)angstrom, b = 10.3625(9)angstrom, c = 11.9562(9)angstrom, alpha = 101.787(7), beta = 91.849(6), and gamma = 102.755(7)degrees, indicating that 4 was crystallized in the triclinic crystal system. The cooperative non-covalent interactions are also discussed with the aid of Hirshfeld surface analysis. The H horizontal ellipsis H, H horizontal ellipsis C, and O horizontal ellipsis H interactions have a major contribution in the molecular packing of 4. Moreover, different quantum chemical parameters were computed and discussed based on DFT calculations. The experimental UV/Vis spectra showed two bands at 299 and 234 nm, which were calculated using the TD-DFT method at 286 (f = 0.068) and 226 nm (f = 0.294), respectively. These bands were assigned to HOMO -> LUMO (95%) and HOMO -> LUMO+2 (86%) transitions, respectively.