The solution phase synthesis of diketopiperazine libraries via the Ugi reaction: Novel application of Armstrong's convertible isonitrile.

Christopher Hulme, Matthew M. Morrissette, Francis A. Volz, Christopher J. Burns

Research output: Contribution to journalArticle

112 Citations (Scopus)

Abstract

This communication describes the generation of high-yielding solution phase diketopiperazine libraries via a '3-step, 1-pot' procedure, employing the Ugi multi-component reaction (MCR), followed by BOC deprotection and cyclization to diketopiperazine (DKP). Exploitation of Armstrong's convertible isonitrile in the Ugi reaction utilising an 'internal nucleophile' approach for diketopiperazine formation is presented.

Original languageEnglish (US)
Pages (from-to)1113-1116
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number10
DOIs
StatePublished - Mar 5 1998
Externally publishedYes

Fingerprint

Diketopiperazines
Nucleophiles
Cyclization
Communication

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

The solution phase synthesis of diketopiperazine libraries via the Ugi reaction : Novel application of Armstrong's convertible isonitrile. / Hulme, Christopher; Morrissette, Matthew M.; Volz, Francis A.; Burns, Christopher J.

In: Tetrahedron Letters, Vol. 39, No. 10, 05.03.1998, p. 1113-1116.

Research output: Contribution to journalArticle

Hulme, Christopher ; Morrissette, Matthew M. ; Volz, Francis A. ; Burns, Christopher J. / The solution phase synthesis of diketopiperazine libraries via the Ugi reaction : Novel application of Armstrong's convertible isonitrile. In: Tetrahedron Letters. 1998 ; Vol. 39, No. 10. pp. 1113-1116.
@article{13d0eabfd653400a886735590b87b85b,
title = "The solution phase synthesis of diketopiperazine libraries via the Ugi reaction: Novel application of Armstrong's convertible isonitrile.",
abstract = "This communication describes the generation of high-yielding solution phase diketopiperazine libraries via a '3-step, 1-pot' procedure, employing the Ugi multi-component reaction (MCR), followed by BOC deprotection and cyclization to diketopiperazine (DKP). Exploitation of Armstrong's convertible isonitrile in the Ugi reaction utilising an 'internal nucleophile' approach for diketopiperazine formation is presented.",
author = "Christopher Hulme and Morrissette, {Matthew M.} and Volz, {Francis A.} and Burns, {Christopher J.}",
year = "1998",
month = "3",
day = "5",
doi = "10.1016/S0040-4039(97)10795-X",
language = "English (US)",
volume = "39",
pages = "1113--1116",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "10",

}

TY - JOUR

T1 - The solution phase synthesis of diketopiperazine libraries via the Ugi reaction

T2 - Novel application of Armstrong's convertible isonitrile.

AU - Hulme, Christopher

AU - Morrissette, Matthew M.

AU - Volz, Francis A.

AU - Burns, Christopher J.

PY - 1998/3/5

Y1 - 1998/3/5

N2 - This communication describes the generation of high-yielding solution phase diketopiperazine libraries via a '3-step, 1-pot' procedure, employing the Ugi multi-component reaction (MCR), followed by BOC deprotection and cyclization to diketopiperazine (DKP). Exploitation of Armstrong's convertible isonitrile in the Ugi reaction utilising an 'internal nucleophile' approach for diketopiperazine formation is presented.

AB - This communication describes the generation of high-yielding solution phase diketopiperazine libraries via a '3-step, 1-pot' procedure, employing the Ugi multi-component reaction (MCR), followed by BOC deprotection and cyclization to diketopiperazine (DKP). Exploitation of Armstrong's convertible isonitrile in the Ugi reaction utilising an 'internal nucleophile' approach for diketopiperazine formation is presented.

UR - http://www.scopus.com/inward/record.url?scp=0032485439&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0032485439&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(97)10795-X

DO - 10.1016/S0040-4039(97)10795-X

M3 - Article

AN - SCOPUS:0032485439

VL - 39

SP - 1113

EP - 1116

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 10

ER -