Structures of Saturated 5H-Pyrrolo[1,2-a][3,1]benzoxazin-1(2H)-ones Prepared from 4-Oxopentanoic Acid and Cyclic Amino Alcohols

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‐(hydroxyme...

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Bibliographic Details
Published in:European journal of organic chemistry 2003-05, Vol.2003 (10), p.1879-1886
Main Authors: Kivelä, Henri, Klika, Karel D., Szabó, Angela, Stájer, Géza, Pihlaja, Kalevi
Format: Article
Language:English
Subjects:
Fused-ring systems
Heterocycles
NMR spectroscopy
Structure elucidation
Online Access:Get full text
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Summary: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 ‐hept‐5‐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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200200662