Novel safety-catch linker and its application with a Ugi/De- BOC/cyclization (UDC) strategy to access carboxylic acids, 1,4- benzodiazepines, diketopiperazines, ketopiperazines and dihydroquinoxalinones

Christopher Hulme; John Peng; George Morton; Joseph M. Salvino; Tim Herpin; Richard Labaudiniere

doi:10.1016/S0040-4039(98)01593-7

Novel safety-catch linker and its application with a Ugi/De- BOC/cyclization (UDC) strategy to access carboxylic acids, 1,4- benzodiazepines, diketopiperazines, ketopiperazines and dihydroquinoxalinones

Christopher Hulme
, John Peng
, George Morton
, Joseph M. Salvino
, Tim Herpin
, Richard Labaudiniere

Research output: Contribution to journal › Article › peer-review

137 Scopus citations

Abstract

This communication reveals the synthesis and application of a novel resin bound isonitrile. The resin is an example of a novel safety-catch linker which upon BOC-activation can be resin cleaved with a variety of nucleophiles. Use of this polymer supported isonitrile in the Ugi multi- component reaction (MCR), followed by resin clipping and cyclization allows access to diverse arrays of 1,4-benzodiazepine-2,5-diones, diketopiperazines and ketopiperazines respectively. The methoxide safety-catch clipping strategy and subsequent solution phase cyclization offers similar advantages to a traceless linker.

Original language	English (US)
Pages (from-to)	7227-7230
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	40
DOIs	https://doi.org/10.1016/S0040-4039(98)01593-7
State	Published - Oct 1 1998
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(98)01593-7

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Hulme, C., Peng, J., Morton, G., Salvino, J. M., Herpin, T., & Labaudiniere, R. (1998). Novel safety-catch linker and its application with a Ugi/De- BOC/cyclization (UDC) strategy to access carboxylic acids, 1,4- benzodiazepines, diketopiperazines, ketopiperazines and dihydroquinoxalinones. Tetrahedron Letters, 39(40), 7227-7230. https://doi.org/10.1016/S0040-4039(98)01593-7

Novel safety-catch linker and its application with a Ugi/De- BOC/cyclization (UDC) strategy to access carboxylic acids, 1,4- benzodiazepines, diketopiperazines, ketopiperazines and dihydroquinoxalinones. / Hulme, Christopher; Peng, John; Morton, George et al.
In: Tetrahedron Letters, Vol. 39, No. 40, 01.10.1998, p. 7227-7230.

Research output: Contribution to journal › Article › peer-review

Hulme, C, Peng, J, Morton, G, Salvino, JM, Herpin, T & Labaudiniere, R 1998, 'Novel safety-catch linker and its application with a Ugi/De- BOC/cyclization (UDC) strategy to access carboxylic acids, 1,4- benzodiazepines, diketopiperazines, ketopiperazines and dihydroquinoxalinones', Tetrahedron Letters, vol. 39, no. 40, pp. 7227-7230. https://doi.org/10.1016/S0040-4039(98)01593-7

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Novel safety-catch linker and its application with a Ugi/De- BOC/cyclization (UDC) strategy to access carboxylic acids, 1,4- benzodiazepines, diketopiperazines, ketopiperazines and dihydroquinoxalinones

Abstract

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