Efficient and mild microwave-assisted stepwise functionalization of naphthalenediimide with alpha-amino acids.
Microwave dielectric heating proved to be an efficient method for the one-pot and stepwise syntheses of symmetrical and unsymmetrical naphthalenediimide derivatives of alpha-amino acids. Acid-labile side chain protecting groups are stable under the reaction conditions; protection of the alpha-carboxylic group is not required. The stepwise condensation of different amino acids resulted in high yields of unsymmetrical naphthalenediimides. The reaction proceeds without racemization and is essentially quantitative.
Pengo
Paolo
P
University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, United Kingdom.
Pantos
G Dan
GD
Otto
Sijbren
S
Sanders
Jeremy K M
JK
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D018360:Crystallography, X-Ray; D007094:Imides; D009682:Magnetic Resonance Spectroscopy; D008872:Microwaves; D015394:Molecular Structure; D009281:Naphthalenes; D010618:Phenanthrolines / Q000737:chemistry*
D000596:Amino Acids; D007094:Imides; D009281:Naphthalenes; D010618:Phenanthrolines; C542131:naphthalenediimide