Efficient and mild microwave-assisted stepwise functionalization of naphthalenediimide with alpha-amino acids

Paolo Pengo; G. Dan Pantos; Sijbren Otto; Jeremy K. M. Sanders

doi:10.1021/jo061195h

Efficient and mild microwave-assisted stepwise functionalization of naphthalenediimide with alpha-amino acids

Paolo Pengo, G. Dan Pantos, Sijbren Otto, Jeremy K. M. Sanders

Research output: Contribution to journal › Article

52 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	7063-7066
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	71
Issue number	18
DOIs	https://doi.org/10.1021/jo061195h
Publication status	Published - 1 Sep 2006

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title = "Efficient and mild microwave-assisted stepwise functionalization of naphthalenediimide with alpha-amino acids",

abstract = "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.",

author = "Paolo Pengo and Pantos, {G. Dan} and Sijbren Otto and Sanders, {Jeremy K. M.}",

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AU - Pengo, Paolo

AU - Pantos, G. Dan

AU - Otto, Sijbren

AU - Sanders, Jeremy K. M.

PY - 2006/9/1

Y1 - 2006/9/1

N2 - 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.

AB - 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.

U2 - 10.1021/jo061195h

DO - 10.1021/jo061195h

M3 - Article

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JO - Journal of Organic Chemistry

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