Nitrogen bridgehead compounds part 90.1 An efficient versatile synthesis of 1-methyl-2-substituted 1,2,3,4-tetrahydro-6H-pyrazino[2,1-b]quinazoline-3,6-diones

J. Kökösi, János Almási, Benjamin Podányi, Miklós Fehér, Zsolt Böcskei, Kálmán Simon, I. Hermecz

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Abstract

A versatile synthesis of 2-substituted 1-methyl- and 1,4-dimethyl-1,2,3,4-tetrahydro-6H-pyrazino[2,1-b]quinazoline-3,6-diones is presented, starting from 2-(1-bromoethyl)quinazolin-4(3H)-one. The key step of the reaction sequence is the diastereoselective cyclization of 2-{[1-(N-2-haloacyl-N-substituted amino]ethyl}quinazolin-4(3H)-ones. Usually 1,4-dimethyl derivatives are obtained as pure racemic cis-compounds (2-alkyl and 2-benzyl derivatives), or a mixture of diastereomers, containing the 4-methyl group in quasiaxial position.

Original languageEnglish
Pages (from-to)1851-1866
Number of pages16
JournalHeterocycles
Volume48
Issue number9
Publication statusPublished - 1998

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Quinazolines
Nitrogen Compounds
Derivatives
Cyclization
4-hydroxyquinazoline

ASJC Scopus subject areas

  • Organic Chemistry

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Nitrogen bridgehead compounds part 90.1 An efficient versatile synthesis of 1-methyl-2-substituted 1,2,3,4-tetrahydro-6H-pyrazino[2,1-b]quinazoline-3,6-diones. / Kökösi, J.; Almási, János; Podányi, Benjamin; Fehér, Miklós; Böcskei, Zsolt; Simon, Kálmán; Hermecz, I.

In: Heterocycles, Vol. 48, No. 9, 1998, p. 1851-1866.

Research output: Contribution to journalArticle

Kökösi, J. ; Almási, János ; Podányi, Benjamin ; Fehér, Miklós ; Böcskei, Zsolt ; Simon, Kálmán ; Hermecz, I. / Nitrogen bridgehead compounds part 90.1 An efficient versatile synthesis of 1-methyl-2-substituted 1,2,3,4-tetrahydro-6H-pyrazino[2,1-b]quinazoline-3,6-diones. In: Heterocycles. 1998 ; Vol. 48, No. 9. pp. 1851-1866.
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abstract = "A versatile synthesis of 2-substituted 1-methyl- and 1,4-dimethyl-1,2,3,4-tetrahydro-6H-pyrazino[2,1-b]quinazoline-3,6-diones is presented, starting from 2-(1-bromoethyl)quinazolin-4(3H)-one. The key step of the reaction sequence is the diastereoselective cyclization of 2-{[1-(N-2-haloacyl-N-substituted amino]ethyl}quinazolin-4(3H)-ones. Usually 1,4-dimethyl derivatives are obtained as pure racemic cis-compounds (2-alkyl and 2-benzyl derivatives), or a mixture of diastereomers, containing the 4-methyl group in quasiaxial position.",
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