Synthesis and structure of cycloalkane- and norbornane-condensed 6-aryl-1,2,4,5-tetrahydropyridazinones

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Abstract

The C=N double bond of certain cis- or trans-cycloalkane and diexo- or diendo-norbornane-condensed pyridazinones was reduced with NaBH3CN. The cis- or trans nature of the starting cycloalkane derivatives was always retained in the saturated products, with a high degree of diastereoselectivity: the hydrogen on the new stereocenter and the annelational hydrogen next to the carbonyl always exhibited the same steric orientation. The stereostructures were determined by means of nmr measurements and confirmed by molecular modelling.

Original languageEnglish
Pages (from-to)259-261
Number of pages3
JournalJournal of Heterocyclic Chemistry
Volume41
Issue number2
Publication statusPublished - Mar 2004

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Norbornanes
Cycloparaffins
Hydrogen
Molecular modeling
Derivatives

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Synthesis and structure of cycloalkane- and norbornane-condensed 6-aryl-1,2,4,5-tetrahydropyridazinones",
abstract = "The C=N double bond of certain cis- or trans-cycloalkane and diexo- or diendo-norbornane-condensed pyridazinones was reduced with NaBH3CN. The cis- or trans nature of the starting cycloalkane derivatives was always retained in the saturated products, with a high degree of diastereoselectivity: the hydrogen on the new stereocenter and the annelational hydrogen next to the carbonyl always exhibited the same steric orientation. The stereostructures were determined by means of nmr measurements and confirmed by molecular modelling.",
author = "Ferenc Csende and A. Het{\'e}nyi and G. St{\'a}jer and F. F{\"u}l{\"o}p",
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language = "English",
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pages = "259--261",
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T1 - Synthesis and structure of cycloalkane- and norbornane-condensed 6-aryl-1,2,4,5-tetrahydropyridazinones

AU - Csende, Ferenc

AU - Hetényi, A.

AU - Stájer, G.

AU - Fülöp, F.

PY - 2004/3

Y1 - 2004/3

N2 - The C=N double bond of certain cis- or trans-cycloalkane and diexo- or diendo-norbornane-condensed pyridazinones was reduced with NaBH3CN. The cis- or trans nature of the starting cycloalkane derivatives was always retained in the saturated products, with a high degree of diastereoselectivity: the hydrogen on the new stereocenter and the annelational hydrogen next to the carbonyl always exhibited the same steric orientation. The stereostructures were determined by means of nmr measurements and confirmed by molecular modelling.

AB - The C=N double bond of certain cis- or trans-cycloalkane and diexo- or diendo-norbornane-condensed pyridazinones was reduced with NaBH3CN. The cis- or trans nature of the starting cycloalkane derivatives was always retained in the saturated products, with a high degree of diastereoselectivity: the hydrogen on the new stereocenter and the annelational hydrogen next to the carbonyl always exhibited the same steric orientation. The stereostructures were determined by means of nmr measurements and confirmed by molecular modelling.

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