Saturated heterocycles. Part 1893

Synthesis and stereochemistry of 2,3-disubstituted 2,5,6,10B-tetrahydroimidazo[5,1-a]isoquinolin-1-ones

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Abstract

The reactions of 1-hydrazido-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (4) with symmetric ketones resulted in imidazo[5,1-a]isoquinolin-1-ones 6a, b via the hydrazone intermediates 5a, b. With aromatic aldehydes, 4 gave diastereomeric pairs of imidazoisoquinolines 8 and 9a, b. The relative configurations and conformations were determined by means of 1H and 13C NMR spectroscopy and DNOE experiments. It was found that, depending on the configuration and bulkiness of the C-3 substituents, trans, cis1-A or cis1-B conformations predominate.

Original languageEnglish
Pages (from-to)168-171
Number of pages4
JournalPharmazie
Volume47
Issue number3
Publication statusPublished - 1992

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Hydrazones
Stereochemistry
Ketones
Aldehydes
Conformations
Magnetic Resonance Spectroscopy
Nuclear magnetic resonance spectroscopy
Experiments
Proton Magnetic Resonance Spectroscopy
Carbon-13 Magnetic Resonance Spectroscopy
heliamine

ASJC Scopus subject areas

  • Molecular Medicine
  • Chemistry(all)
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science
  • Pharmacology

Cite this

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title = "Saturated heterocycles. Part 1893: Synthesis and stereochemistry of 2,3-disubstituted 2,5,6,10B-tetrahydroimidazo[5,1-a]isoquinolin-1-ones",
abstract = "The reactions of 1-hydrazido-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (4) with symmetric ketones resulted in imidazo[5,1-a]isoquinolin-1-ones 6a, b via the hydrazone intermediates 5a, b. With aromatic aldehydes, 4 gave diastereomeric pairs of imidazoisoquinolines 8 and 9a, b. The relative configurations and conformations were determined by means of 1H and 13C NMR spectroscopy and DNOE experiments. It was found that, depending on the configuration and bulkiness of the C-3 substituents, trans, cis1-A or cis1-B conformations predominate.",
author = "F. F{\"u}l{\"o}p and E. Semega and G. Bern{\'a}th and P. Soh{\'a}r",
year = "1992",
language = "English",
volume = "47",
pages = "168--171",
journal = "Die Pharmazie",
issn = "0031-7144",
publisher = "Govi-Verlag Pharmazeutischer Verlag GmbH",
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T1 - Saturated heterocycles. Part 1893

T2 - Synthesis and stereochemistry of 2,3-disubstituted 2,5,6,10B-tetrahydroimidazo[5,1-a]isoquinolin-1-ones

AU - Fülöp, F.

AU - Semega, E.

AU - Bernáth, G.

AU - Sohár, P.

PY - 1992

Y1 - 1992

N2 - The reactions of 1-hydrazido-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (4) with symmetric ketones resulted in imidazo[5,1-a]isoquinolin-1-ones 6a, b via the hydrazone intermediates 5a, b. With aromatic aldehydes, 4 gave diastereomeric pairs of imidazoisoquinolines 8 and 9a, b. The relative configurations and conformations were determined by means of 1H and 13C NMR spectroscopy and DNOE experiments. It was found that, depending on the configuration and bulkiness of the C-3 substituents, trans, cis1-A or cis1-B conformations predominate.

AB - The reactions of 1-hydrazido-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (4) with symmetric ketones resulted in imidazo[5,1-a]isoquinolin-1-ones 6a, b via the hydrazone intermediates 5a, b. With aromatic aldehydes, 4 gave diastereomeric pairs of imidazoisoquinolines 8 and 9a, b. The relative configurations and conformations were determined by means of 1H and 13C NMR spectroscopy and DNOE experiments. It was found that, depending on the configuration and bulkiness of the C-3 substituents, trans, cis1-A or cis1-B conformations predominate.

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