Efficient Preparation of Photolabile Agent MNI-glu by Regioselective Nitration of 4-Methoxyindoline Derivative

Abstract

The present work investigates the nitration of 4-methoxy indoline derivative with different reagents and optimized conditions. We now report a simple methodology for nitration employing claycop in the presence of amine, which offers significant improvement with regard to the yield and regioselectivity, and a much more favorable isomeric ratio of products was obtained under mild conditions. Therefore, a useful method for preparation of a photolabile L-glutamate derivative was concurrently established.

Keywords:

• Aromatic nitration
• caged L-glutamate
• claypop
• nitroindolines
• photorelease agent

ACKNOWLEDGMENTS

We thank the National Science Foundation of China and 985 Program of the Ministry of Education of China for financial support.

Notes

^a The molar ratio was calculated as the amount of nitrate anion contained in claycop.

^a The molar ratios were calculated as the amount of nitrate anion contained in claycop.