Microwave Synthesis of Chiral N-Benzyl-2-methyl-2H-benzo[b][1,4]oxazin/thiazin-3(4H)-ones via Smiles Rearrangement and their Biological Evaluation

Microwave-assisted synthesis of optically active N-substituted 2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-ones and -thiazin-3(4H)-ones via Smiles rearrangement

“…The optical activities of final products indicate that O-or S-alkylation takes place via S N 2 process. 37 The gas chromatography-MS spectra of all the corresponding products clearly indicated the formation of the corresponding product, and IR, 1 …”

DOTMA-based amides (DOTMAMs) as a platform for the development of PARACEST MRI contrast agents

“…A DCC-mediated peptide coupling between (S)-2chloropropionic acid (12, Scheme 1) and benzylamine afforded corresponding secondary chloroderivative 13 (Scheme 1) in good yield using a modified literature procedure. 20 Despite the use of 2-chloropropionic acid derivatives previously for the preparation of DOTMA, 15 the reactivity of electrophile 13 was found to be insufficient to achieve the peralkylation of cyclen. Therefore, we turned our attention to the use of (S)-lactic acid derived pseudohalides as potential electrophiles.…”

“…The reaction was carried out as described in the literature, 34 starting from 430 μL (5 mmol) of S-chloropropionic acid (12 (14).…”