Structures of saturated 5H-Pyrrolo[1,2-a][3,1]benzoxazin-1(2H)-ones prepared from 4-oxopentanoic acid and cyclic amino alcohols

Henri Kivelä, Karel D. Klika, Angela Szabó, G. Stájer, Kalevi Pihlaja

Research output: Article

3 Citations (Scopus)

Abstract

Saturated heterocycles containing two condensed heterocyclic rings and a carbo(bi)cyclic ring have been prepared by the reaction of 4-oxopentanoic acid (1) with (bi)cyclic amino alcohols. 5H-Pyrrolo[1,2-a][3,1]benzoxazin-1(2H)-ones 2-5 were formed in the reaction of 1 with trans- or cis-2-(hydroxymethyl)cyclohexylamines or -cyclohexenylamines. With di-endo- or di-exo-3-aminobicyclo[2.2.1]hept-2-yl- or -hept5-en-2-ylmethanols, 1 yielded the corresponding derivatives 6-9 that are methylene-bridged in the cyclohexane or cyclohexene rings. The stereoselectivity of the syntheses were high; only for 5, 7 and 9 were both C-3a epimers produced in observable amounts. The structures were established by means of NMR spectroscopic methods by applying standard pulse techniques.

Original languageEnglish
Pages (from-to)1879-1886
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number10
Publication statusPublished - máj. 2003

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Cyclohexylamines
Amino Alcohols
Stereoselectivity
Charcoal
Nuclear magnetic resonance
Derivatives
Cyclohexane
cyclohexene
4-oxopentanoic acid

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Structures of saturated 5H-Pyrrolo[1,2-a][3,1]benzoxazin-1(2H)-ones prepared from 4-oxopentanoic acid and cyclic amino alcohols. / Kivelä, Henri; Klika, Karel D.; Szabó, Angela; Stájer, G.; Pihlaja, Kalevi.

In: European Journal of Organic Chemistry, No. 10, 05.2003, p. 1879-1886.

Research output: Article

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AU - Klika, Karel D.

AU - Szabó, Angela

AU - Stájer, G.

AU - Pihlaja, Kalevi

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N2 - Saturated heterocycles containing two condensed heterocyclic rings and a carbo(bi)cyclic ring have been prepared by the reaction of 4-oxopentanoic acid (1) with (bi)cyclic amino alcohols. 5H-Pyrrolo[1,2-a][3,1]benzoxazin-1(2H)-ones 2-5 were formed in the reaction of 1 with trans- or cis-2-(hydroxymethyl)cyclohexylamines or -cyclohexenylamines. With di-endo- or di-exo-3-aminobicyclo[2.2.1]hept-2-yl- or -hept5-en-2-ylmethanols, 1 yielded the corresponding derivatives 6-9 that are methylene-bridged in the cyclohexane or cyclohexene rings. The stereoselectivity of the syntheses were high; only for 5, 7 and 9 were both C-3a epimers produced in observable amounts. The structures were established by means of NMR spectroscopic methods by applying standard pulse techniques.

AB - Saturated heterocycles containing two condensed heterocyclic rings and a carbo(bi)cyclic ring have been prepared by the reaction of 4-oxopentanoic acid (1) with (bi)cyclic amino alcohols. 5H-Pyrrolo[1,2-a][3,1]benzoxazin-1(2H)-ones 2-5 were formed in the reaction of 1 with trans- or cis-2-(hydroxymethyl)cyclohexylamines or -cyclohexenylamines. With di-endo- or di-exo-3-aminobicyclo[2.2.1]hept-2-yl- or -hept5-en-2-ylmethanols, 1 yielded the corresponding derivatives 6-9 that are methylene-bridged in the cyclohexane or cyclohexene rings. The stereoselectivity of the syntheses were high; only for 5, 7 and 9 were both C-3a epimers produced in observable amounts. The structures were established by means of NMR spectroscopic methods by applying standard pulse techniques.

KW - Fused-ring systems

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KW - Structure elucidation

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