Synthesis of 1, 5-Disubstituted Tetrazole via Ugi Azide Reaction: An Asymmetric Induction Approach

摘要

abstract_textpThe Ugi-azide reaction of an enantiopure amino acid derived isocyanides, amino acid esters, aldehydes and TMS-N-3 in MeOH: THF solvent system at 50 degrees C yielded peptidomimetics comprising tetrazole as amide bond isostere. Both N-terminal (alpha-isocyanoesters) and C-terminal isocyanides (N-beta-Cbz-protected amino alkyl isocyanides) have been employed to yield diversified tetrazole peptidomimetics, having the possibility of further derivatization through either N- or C-terminal chain elongation. Ugi-azide reaction is a isocyanide based multi-component reaction (IMCR), as a result, change in amino acid derived isocyanides had given structurally diverse products of biological interest. Good yields of products were obtained after column purification and were stable for shelf storage. The products are novel and were well characterized by Mass, (HNMR)-H-1 and (CNMR)-C-13 spectral studies. The present method offers several advantages such as one-pot simple procedure, high yields and easy purification of products./p/abstract_text