The reaction of N-isocyaniminotriphenylphosphorane (NICITPP) with 2-oxopropyl-1-benzenecarbothioate and a primary amine in the presence of benzoic acid derivatives

GRAPHICAL ABSTRACT

ABSTRACT

Reactions of N-isocyaniminotriphenylphosphorane (NICITPP) with 2-oxopropyl-1-benzenecarbothioate in the presence of aromatic carboxylic acids and primary amines proceed smoothly at room temperature (18–26°C) and in neutral conditions to afford sterically congested 1,3,4-oxadiazole derivatives in high yields. The reaction progresses smoothly and clearly under mild conditions and no side reactions were observed.

Keywords:

• N-isocyanimino-triphenylphosphorane (NICITPP)
• 2-oxopropyl-1-benzenecarbothioate
• aromatic carboxylic acid
• primary amine
• 1,3,4-oxadiazole
• aza-Wittig reaction

Funding

This work is funded by the grant NRF-2015-002423 of the National Research Foundation of Korea.