Convenient, Microwave-Assisted, One-Pot Synthesis of Photochromic Fulgimides Bearing Reactive Groups

Abstract

A convenient, microwave-assisted, one-pot synthesis of the fulgimides (3) bearing reactive groups on N-substituents from the corresponding fulgides (1a–d) and amines (2a–e) is described. The synthesis provided the functionalized fulgimides (3) in yields of 50–84% under microwave irradiation within 25 min in the presence of 4-dimethylaminopyridine (DMAP) and dicyclohexylcarbodiimide (DCC).

Keywords:

• Fulgide
• functionalized fulgimide
• microwave-assisted
• one-pot synthesis
• photochromic

ACKNOWLEDGMENT

The financial support from the Key Program of Science and Technology in Hebei Province (05547001D-1) is gratefully acknowledged.

Notes

^a One-pot reaction, step A: fulgide (1d) (0.1 mmol), p-aminobenzoic acid (2a), and DMAP (0.01 mmol) in pyridine 1.0 mL; step B: DCC (0.1 mmol) was added.

^b Solvents: xylene (0.8 mL) and diglyme (0.2 mL).

^c Solvent: diglyme (1.0 mL).

^a One-pot reaction conditions, A: fulgides (1) (0.1 mmol), amines (2) (0.4 mmol) and DMAP (0.01 mmol) in pyridine 1.0 mL, MW, 180°C, 10 min.; B: DCC (0.1 mmol) was added, MW, 140°C, 15 min.

^b Xylene (1.0 mL) was used as the solvent.