Tetramic acid and imidazolidinone syntheses via unexpected base induced cyclisations of alanine derived Weinreb amides

Colin Gibson, A.R. Kennedy, R.R. Morthala, J.A. Parkinson, C.J. Suckling

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Reactions of N-protected derivatives of Weinreb amides of alanine with strong base unexpectedly gave tetramic acid derivatives or an imidazolidinone. The tetramic acid derivatives were obtained by unusual cyclisation of N-acyl N-methoxy derivatives of alanine Weinreb amide upon treatment with potassium hexamethyldisilazide and benzyl bromide. In contrast, treatment of a bromobenzylidine alanine Weinreb amide with potassium hexamethyldisilazide gave rise to cyclisation to form an imidazolidinone.
LanguageEnglish
Pages7619-7625
Number of pages7
JournalTetrahedron
Volume64
Issue number32
DOIs
Publication statusPublished - 4 Aug 2008

Fingerprint

Cyclization
Amides
Alanine
Derivatives
Potassium
tetramic acid

Keywords

  • Weinreb amides
  • tetramic acid
  • imidazolidinone

Cite this

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abstract = "Reactions of N-protected derivatives of Weinreb amides of alanine with strong base unexpectedly gave tetramic acid derivatives or an imidazolidinone. The tetramic acid derivatives were obtained by unusual cyclisation of N-acyl N-methoxy derivatives of alanine Weinreb amide upon treatment with potassium hexamethyldisilazide and benzyl bromide. In contrast, treatment of a bromobenzylidine alanine Weinreb amide with potassium hexamethyldisilazide gave rise to cyclisation to form an imidazolidinone.",
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Tetramic acid and imidazolidinone syntheses via unexpected base induced cyclisations of alanine derived Weinreb amides. / Gibson, Colin; Kennedy, A.R.; Morthala, R.R.; Parkinson, J.A.; Suckling, C.J.

In: Tetrahedron, Vol. 64, No. 32, 04.08.2008, p. 7619-7625.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Tetramic acid and imidazolidinone syntheses via unexpected base induced cyclisations of alanine derived Weinreb amides

AU - Gibson, Colin

AU - Kennedy, A.R.

AU - Morthala, R.R.

AU - Parkinson, J.A.

AU - Suckling, C.J.

PY - 2008/8/4

Y1 - 2008/8/4

N2 - Reactions of N-protected derivatives of Weinreb amides of alanine with strong base unexpectedly gave tetramic acid derivatives or an imidazolidinone. The tetramic acid derivatives were obtained by unusual cyclisation of N-acyl N-methoxy derivatives of alanine Weinreb amide upon treatment with potassium hexamethyldisilazide and benzyl bromide. In contrast, treatment of a bromobenzylidine alanine Weinreb amide with potassium hexamethyldisilazide gave rise to cyclisation to form an imidazolidinone.

AB - Reactions of N-protected derivatives of Weinreb amides of alanine with strong base unexpectedly gave tetramic acid derivatives or an imidazolidinone. The tetramic acid derivatives were obtained by unusual cyclisation of N-acyl N-methoxy derivatives of alanine Weinreb amide upon treatment with potassium hexamethyldisilazide and benzyl bromide. In contrast, treatment of a bromobenzylidine alanine Weinreb amide with potassium hexamethyldisilazide gave rise to cyclisation to form an imidazolidinone.

KW - Weinreb amides

KW - tetramic acid

KW - imidazolidinone

U2 - 10.1016/j.tet.2008.05.058

DO - 10.1016/j.tet.2008.05.058

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T2 - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

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