Preparation and structure of pyrrolo[2,1-b]- and isoindolo[1,2-b][3,1]epoxyquinazolines

Iván Kanizsai, Ferenc Miklós, P. Sohár, A. Csámpai, Reijo Sillanpää, G. Stájer

Research output: Article

4 Citations (Scopus)

Abstract

Various γ-oxocarboxylic acids [aroylpropionic acids, cis-2-(4-methylbenzoyl)cyclohexanecarboxylic acid, diendo-3-benzoylbicyclo[2.2.1] heptane-2-carboxylic acid, formylbenzoic acid, methanobenzenecyclooctencarboxylic acid and the cyclopentadiene adduct of 3-trans-(4-methylbenzoyl)acrylic acid] were reacted with diexo-3-aminomethyl-7-oxabicyclo[2.2.1]hept-5-en-2-ylamine 2 to result in condensed pyrroloepoxyquinazolines 3-10. The starting 2 retained the diexo configuration, but cis → trans isomerization took place when cis-2-(4-methylbenzoyl)cyclohexanecarboxylic acid was applied. The structures, including the ring annelations and the position of the aryl group on the new chiral centre, were established by means of NMR spectroscopy, and in the cases of the trans-3-(4-methylbenzoyl)acrylic acid-cyclopentadiene adduct for 10a, 10b and 10c by X-ray crystallography.

Original languageEnglish
Pages (from-to)37-45
Number of pages9
JournalJournal of Molecular Structure
Volume831
Issue number1-3
DOIs
Publication statusPublished - ápr. 17 2007

Fingerprint

Cyclopentanes
NSC 153174
preparation
acids
Acids
Heptanes
X ray crystallography
X Ray Crystallography
acrylic acid
Isomerization
Carboxylic Acids
Nuclear magnetic resonance spectroscopy
adducts
Magnetic Resonance Spectroscopy
Acrylics
heptanes
carboxylic acids
isomerization
crystallography
Heptane

ASJC Scopus subject areas

  • Structural Biology
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Atomic and Molecular Physics, and Optics
  • Materials Science (miscellaneous)

Cite this

Preparation and structure of pyrrolo[2,1-b]- and isoindolo[1,2-b][3,1]epoxyquinazolines. / Kanizsai, Iván; Miklós, Ferenc; Sohár, P.; Csámpai, A.; Sillanpää, Reijo; Stájer, G.

In: Journal of Molecular Structure, Vol. 831, No. 1-3, 17.04.2007, p. 37-45.

Research output: Article

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AU - Kanizsai, Iván

AU - Miklós, Ferenc

AU - Sohár, P.

AU - Csámpai, A.

AU - Sillanpää, Reijo

AU - Stájer, G.

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AB - Various γ-oxocarboxylic acids [aroylpropionic acids, cis-2-(4-methylbenzoyl)cyclohexanecarboxylic acid, diendo-3-benzoylbicyclo[2.2.1] heptane-2-carboxylic acid, formylbenzoic acid, methanobenzenecyclooctencarboxylic acid and the cyclopentadiene adduct of 3-trans-(4-methylbenzoyl)acrylic acid] were reacted with diexo-3-aminomethyl-7-oxabicyclo[2.2.1]hept-5-en-2-ylamine 2 to result in condensed pyrroloepoxyquinazolines 3-10. The starting 2 retained the diexo configuration, but cis → trans isomerization took place when cis-2-(4-methylbenzoyl)cyclohexanecarboxylic acid was applied. The structures, including the ring annelations and the position of the aryl group on the new chiral centre, were established by means of NMR spectroscopy, and in the cases of the trans-3-(4-methylbenzoyl)acrylic acid-cyclopentadiene adduct for 10a, 10b and 10c by X-ray crystallography.

KW - Diastereoisomers

KW - DIFFNOE

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KW - Isoindoloepoxyquinazolines

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KW - Pyrroloepoxyquinazolines

KW - X-ray

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