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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2009 - Issue 1
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Original Articles

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

, , , &
Pages 157-166 | Received 09 Aug 2008, Published online: 15 Dec 2009
 

Abstract

A convenient, microwave-assisted, one-pot synthesis of the fulgimides (3) bearing reactive groups on N-substituents from the corresponding fulgides (1ad) and amines (2ae) 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).

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.

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