NMR and X-ray structural study of saturated (p-chlorophenyl)-pyrrolo[1,2-a][3,1]benzoxazin-1-ones prepared from aroylisobutyric acid and cyclic amino alcohols. High energy barriers for hindered rotation of bridgehead phenyl groups

Petri Tähtinen, Reijo Sillanpää, G. Stájer, Angela E. Szabó, Kalevi Pihlaja

Research output: Article

8 Citations (Scopus)

Abstract

From 2-methyl-3-(p-chlorobenzoyl)propionic acid with stereoisomeric cyclic saturated or partly saturated cis and trans 1,3-amino alcohols and bicyclic amino alcohols, tri- and tetracyclic methyl substituted (p-chlorophenyl)-pyrrolo[1,2-a][3,1]benzoxazin-1-ones and methylene bridged derivatives were prepared. For comparison, the bicyclic oxazolone and oxazinone analogs were also prepared. In each case isomeric pairs, which differ in the mutual positions of the aryl and methyl groups, were formed. For the methylene bridged derivatives, the isomers were separated. For evaluation of the structure in solution 1H, 13C{1H}, NOE difference, COSY and HMQC NMR methods were used, and for the crystal structure determinations X-ray diffraction measurements were used. An unusually high free energy barrier of the restricted rotation of the bridgehead p-chlorophenyl group was measured for a cis-, a diendo- and a diexo-fused compound.

Original languageEnglish
Pages (from-to)2011-2021
Number of pages11
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number10
Publication statusPublished - okt. 1999

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Amino Alcohols
Energy barriers
Nuclear magnetic resonance
Oxazolone
Derivatives
X rays
Acids
Isomers
Free energy
Crystal structure
X ray diffraction
propionic acid
vitamin B 12 factor III

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "NMR and X-ray structural study of saturated (p-chlorophenyl)-pyrrolo[1,2-a][3,1]benzoxazin-1-ones prepared from aroylisobutyric acid and cyclic amino alcohols. High energy barriers for hindered rotation of bridgehead phenyl groups",
abstract = "From 2-methyl-3-(p-chlorobenzoyl)propionic acid with stereoisomeric cyclic saturated or partly saturated cis and trans 1,3-amino alcohols and bicyclic amino alcohols, tri- and tetracyclic methyl substituted (p-chlorophenyl)-pyrrolo[1,2-a][3,1]benzoxazin-1-ones and methylene bridged derivatives were prepared. For comparison, the bicyclic oxazolone and oxazinone analogs were also prepared. In each case isomeric pairs, which differ in the mutual positions of the aryl and methyl groups, were formed. For the methylene bridged derivatives, the isomers were separated. For evaluation of the structure in solution 1H, 13C{1H}, NOE difference, COSY and HMQC NMR methods were used, and for the crystal structure determinations X-ray diffraction measurements were used. An unusually high free energy barrier of the restricted rotation of the bridgehead p-chlorophenyl group was measured for a cis-, a diendo- and a diexo-fused compound.",
author = "Petri T{\"a}htinen and Reijo Sillanp{\"a}{\"a} and G. St{\'a}jer and Szab{\'o}, {Angela E.} and Kalevi Pihlaja",
year = "1999",
month = "10",
language = "English",
pages = "2011--2021",
journal = "Journal of the Chemical Society, Perkin Transactions 2",
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TY - JOUR

T1 - NMR and X-ray structural study of saturated (p-chlorophenyl)-pyrrolo[1,2-a][3,1]benzoxazin-1-ones prepared from aroylisobutyric acid and cyclic amino alcohols. High energy barriers for hindered rotation of bridgehead phenyl groups

AU - Tähtinen, Petri

AU - Sillanpää, Reijo

AU - Stájer, G.

AU - Szabó, Angela E.

AU - Pihlaja, Kalevi

PY - 1999/10

Y1 - 1999/10

N2 - From 2-methyl-3-(p-chlorobenzoyl)propionic acid with stereoisomeric cyclic saturated or partly saturated cis and trans 1,3-amino alcohols and bicyclic amino alcohols, tri- and tetracyclic methyl substituted (p-chlorophenyl)-pyrrolo[1,2-a][3,1]benzoxazin-1-ones and methylene bridged derivatives were prepared. For comparison, the bicyclic oxazolone and oxazinone analogs were also prepared. In each case isomeric pairs, which differ in the mutual positions of the aryl and methyl groups, were formed. For the methylene bridged derivatives, the isomers were separated. For evaluation of the structure in solution 1H, 13C{1H}, NOE difference, COSY and HMQC NMR methods were used, and for the crystal structure determinations X-ray diffraction measurements were used. An unusually high free energy barrier of the restricted rotation of the bridgehead p-chlorophenyl group was measured for a cis-, a diendo- and a diexo-fused compound.

AB - From 2-methyl-3-(p-chlorobenzoyl)propionic acid with stereoisomeric cyclic saturated or partly saturated cis and trans 1,3-amino alcohols and bicyclic amino alcohols, tri- and tetracyclic methyl substituted (p-chlorophenyl)-pyrrolo[1,2-a][3,1]benzoxazin-1-ones and methylene bridged derivatives were prepared. For comparison, the bicyclic oxazolone and oxazinone analogs were also prepared. In each case isomeric pairs, which differ in the mutual positions of the aryl and methyl groups, were formed. For the methylene bridged derivatives, the isomers were separated. For evaluation of the structure in solution 1H, 13C{1H}, NOE difference, COSY and HMQC NMR methods were used, and for the crystal structure determinations X-ray diffraction measurements were used. An unusually high free energy barrier of the restricted rotation of the bridgehead p-chlorophenyl group was measured for a cis-, a diendo- and a diexo-fused compound.

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