Applications of N-BOC-diamines for the solution phase synthesis of ketopiperazine libraries utilizing a Ugi/De-BOC/Cyclization (UDC) strategy

Christopher Hulme; John Peng; Bonnie Louridas; Paul Menard; Paul Krolikowski; N. Vasant Kumar

doi:10.1016/S0040-4039(98)01770-5

Applications of N-BOC-diamines for the solution phase synthesis of ketopiperazine libraries utilizing a Ugi/De-BOC/Cyclization (UDC) strategy

Christopher Hulme
, John Peng
, Bonnie Louridas
, Paul Menard
, Paul Krolikowski
, N. Vasant Kumar

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

67 Scopus citations

Abstract

This communication reveals a novel application of the 'so-called' convertible isonitrile for the solution phase generation of ketopiperazine libraries. Use of mono N-BOC diamines in the Ugi multi-component reaction (MCR), followed by BOC removal and base treatment (a '3 step, 1-pot procedure') affords ketopiperazines in good yield. The generality of this procedure was further explored revealing novel routes to dihydroquinoxalinones and 1,4-benzodiazepines respectively.

Original language	English (US)
Pages (from-to)	8047-8050
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	44
DOIs	https://doi.org/10.1016/S0040-4039(98)01770-5
State	Published - Oct 29 1998
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(98)01770-5

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abstract = "This communication reveals a novel application of the 'so-called' convertible isonitrile for the solution phase generation of ketopiperazine libraries. Use of mono N-BOC diamines in the Ugi multi-component reaction (MCR), followed by BOC removal and base treatment (a '3 step, 1-pot procedure') affords ketopiperazines in good yield. The generality of this procedure was further explored revealing novel routes to dihydroquinoxalinones and 1,4-benzodiazepines respectively.",

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AU - Hulme, Christopher

AU - Peng, John

AU - Louridas, Bonnie

AU - Menard, Paul

AU - Krolikowski, Paul

AU - Kumar, N. Vasant

PY - 1998/10/29

Y1 - 1998/10/29

N2 - This communication reveals a novel application of the 'so-called' convertible isonitrile for the solution phase generation of ketopiperazine libraries. Use of mono N-BOC diamines in the Ugi multi-component reaction (MCR), followed by BOC removal and base treatment (a '3 step, 1-pot procedure') affords ketopiperazines in good yield. The generality of this procedure was further explored revealing novel routes to dihydroquinoxalinones and 1,4-benzodiazepines respectively.

AB - This communication reveals a novel application of the 'so-called' convertible isonitrile for the solution phase generation of ketopiperazine libraries. Use of mono N-BOC diamines in the Ugi multi-component reaction (MCR), followed by BOC removal and base treatment (a '3 step, 1-pot procedure') affords ketopiperazines in good yield. The generality of this procedure was further explored revealing novel routes to dihydroquinoxalinones and 1,4-benzodiazepines respectively.

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IS - 44

ER -

Applications of N-BOC-diamines for the solution phase synthesis of ketopiperazine libraries utilizing a Ugi/De-BOC/Cyclization (UDC) strategy

Abstract

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