Preparation and steric structure of 3(2 H)-pyridazinones and 1,2-oxazin-6-ones fused with three- to six-membered saturated carbocycles or norbornane skeleton

G. Stájer, F. Csende, G. Bernáth, P. Sohár, J. Szúnyog

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17 Citations (Scopus)

Abstract

Reactions of cis-2-(4-methylbenzoyl)-cyclopropane- (1) and-cyclobutanecarboxylic acids (2), the stereoisomeric cyclohexyl homologues (3 and 4), and di-endo-3-(4-methylbenzoyl)-bi-cyclo-[2.2.1]heptane-2-carboxylic acid (5) with hydrazines yield the cycloalkane-condensed (3(2 H)-pyridazinones 6-9 and the norbornane di-endo-fused derivatives 10. With hydroxylamine, compounds 1 and 3-5 were transformed to the cycloalkane- and norbornane-condensed 1,2-oxazin-6-ones 11-14. Transformation of 3-5 led to the trans-hexahydroanthrone 17a and its methylene-bridged analogue 24. From the stereoisomeric hexahydro-1(3 H)-isobenzofuranones 20 and 21, the partly saturated anthrones were also prepared; the products (16b and 17b) contain the methyl substituent in position 6. On reduction, 16b yield the 2-methyloctahydroanthracene 22. The structures of the compounds were proved by1H and13C NMR spectroscopy, making use of NOE, DEPT, and CH-COSY techniques.

Original languageEnglish
Pages (from-to)933-944
Number of pages12
JournalMonatshefte fur Chemie
Volume125
Issue number8-9
DOIs
Publication statusPublished - Aug 1994

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Norbornanes
Cycloparaffins
Anthracenes
Hydrazines
Heptanes
Hydroxylamine
Carboxylic Acids
Nuclear magnetic resonance spectroscopy
Derivatives
Acids

Keywords

  • Cycloalkanes
  • Friedel-Crafts acylation
  • Heterocycles
  • Isomerization
  • LAH/AlCl
  • Methyloctahydro-anthracen-9-ones
  • Reduction

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Preparation and steric structure of 3(2 H)-pyridazinones and 1,2-oxazin-6-ones fused with three- to six-membered saturated carbocycles or norbornane skeleton",
abstract = "Reactions of cis-2-(4-methylbenzoyl)-cyclopropane- (1) and-cyclobutanecarboxylic acids (2), the stereoisomeric cyclohexyl homologues (3 and 4), and di-endo-3-(4-methylbenzoyl)-bi-cyclo-[2.2.1]heptane-2-carboxylic acid (5) with hydrazines yield the cycloalkane-condensed (3(2 H)-pyridazinones 6-9 and the norbornane di-endo-fused derivatives 10. With hydroxylamine, compounds 1 and 3-5 were transformed to the cycloalkane- and norbornane-condensed 1,2-oxazin-6-ones 11-14. Transformation of 3-5 led to the trans-hexahydroanthrone 17a and its methylene-bridged analogue 24. From the stereoisomeric hexahydro-1(3 H)-isobenzofuranones 20 and 21, the partly saturated anthrones were also prepared; the products (16b and 17b) contain the methyl substituent in position 6. On reduction, 16b yield the 2-methyloctahydroanthracene 22. The structures of the compounds were proved by1H and13C NMR spectroscopy, making use of NOE, DEPT, and CH-COSY techniques.",
keywords = "Cycloalkanes, Friedel-Crafts acylation, Heterocycles, Isomerization, LAH/AlCl, Methyloctahydro-anthracen-9-ones, Reduction",
author = "G. St{\'a}jer and F. Csende and G. Bern{\'a}th and P. Soh{\'a}r and J. Sz{\'u}nyog",
year = "1994",
month = "8",
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T1 - Preparation and steric structure of 3(2 H)-pyridazinones and 1,2-oxazin-6-ones fused with three- to six-membered saturated carbocycles or norbornane skeleton

AU - Stájer, G.

AU - Csende, F.

AU - Bernáth, G.

AU - Sohár, P.

AU - Szúnyog, J.

PY - 1994/8

Y1 - 1994/8

N2 - Reactions of cis-2-(4-methylbenzoyl)-cyclopropane- (1) and-cyclobutanecarboxylic acids (2), the stereoisomeric cyclohexyl homologues (3 and 4), and di-endo-3-(4-methylbenzoyl)-bi-cyclo-[2.2.1]heptane-2-carboxylic acid (5) with hydrazines yield the cycloalkane-condensed (3(2 H)-pyridazinones 6-9 and the norbornane di-endo-fused derivatives 10. With hydroxylamine, compounds 1 and 3-5 were transformed to the cycloalkane- and norbornane-condensed 1,2-oxazin-6-ones 11-14. Transformation of 3-5 led to the trans-hexahydroanthrone 17a and its methylene-bridged analogue 24. From the stereoisomeric hexahydro-1(3 H)-isobenzofuranones 20 and 21, the partly saturated anthrones were also prepared; the products (16b and 17b) contain the methyl substituent in position 6. On reduction, 16b yield the 2-methyloctahydroanthracene 22. The structures of the compounds were proved by1H and13C NMR spectroscopy, making use of NOE, DEPT, and CH-COSY techniques.

AB - Reactions of cis-2-(4-methylbenzoyl)-cyclopropane- (1) and-cyclobutanecarboxylic acids (2), the stereoisomeric cyclohexyl homologues (3 and 4), and di-endo-3-(4-methylbenzoyl)-bi-cyclo-[2.2.1]heptane-2-carboxylic acid (5) with hydrazines yield the cycloalkane-condensed (3(2 H)-pyridazinones 6-9 and the norbornane di-endo-fused derivatives 10. With hydroxylamine, compounds 1 and 3-5 were transformed to the cycloalkane- and norbornane-condensed 1,2-oxazin-6-ones 11-14. Transformation of 3-5 led to the trans-hexahydroanthrone 17a and its methylene-bridged analogue 24. From the stereoisomeric hexahydro-1(3 H)-isobenzofuranones 20 and 21, the partly saturated anthrones were also prepared; the products (16b and 17b) contain the methyl substituent in position 6. On reduction, 16b yield the 2-methyloctahydroanthracene 22. The structures of the compounds were proved by1H and13C NMR spectroscopy, making use of NOE, DEPT, and CH-COSY techniques.

KW - Cycloalkanes

KW - Friedel-Crafts acylation

KW - Heterocycles

KW - Isomerization

KW - LAH/AlCl

KW - Methyloctahydro-anthracen-9-ones

KW - Reduction

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