Synthesis of adamantane appended supramolecular amphiphilic bullets: structural and spectral insights

Abstract

The present manuscript reports the synthesis of two targeted amphiphilic bullets through a highly selective amide bond formation by competing parallel esterification. A simple reaction protocol was developed based on the usage of commercially available starting materials(1-Amino-3-adamantanol), reagents (DIPEA) and solvents (THF). Readily available materials were chosen in this regard. Out of the three reactions, two reactions resulted 100 % atom economy. All these reactions resulted more than 92 % yield of the targeted products via selective amide bond formation. All these reactions Milder reaction conditions such as room temperature and 3hours of reaction time were enough to carryout the process. All the novel products were charactezed by advanced analytical techniques such as 1H, 13C NMR, Infra Red and ESI-MS spectral data. DFT studies were carried out to predict relative stabilities and reactivities of all the three amides. The solavation energy of phthalimide derivative is having relatively higher solvation energy in comparison with that of other amides.In case of relative stabilities, BOC group containig amide is more stable. On the other hand, succinamide deravative is having higher energy gap in between HOMO and LUMO.