Preparation and structure of diexo-oxanorbornane-fused 1,3-heterocycles

Ferenc Miklós, Iván Kanizsai, Steffen Thomas, Erich Kleinpeter, Reijo Sillanpää, Géza Stájer

Research output: Article

15 Citations (Scopus)

Abstract

Via the reaction of diexo-oxanorbornanedicarboxylic anhydride with toluene, the diexo-aroylcarboxylic acid (3a) was prepared, which exists partly as the tautomeric lactol (3b). With bifunctional reagents, 3a yields fused heterocycles containing three-six rings. Thus, alkylenediamines result in imidazole- and 1,3-diazepine-fused oxygen-bridged isoindolones (6a,b), alkanolamines form the oxazole- and 1,3-oxazine-fused oxanorbornene derivatives (7a-c), and o-phenylenediamine undergoes cyclization to furnish the condensed benzimidazole (8). The reaction of 3a with diexo-aminonorbornanecarbohydrazide yields a pyrimidopyridazine containing six condensed rings (9). In a similar reaction with diendo-aminonorbornenecarbohydrazide, cyclopentadiene cleaves off to give the tricyclic retro Diels-Alder product (10). The structures, and particulary the configurations at the oxanorbornane ring systems and the position of the aryl substituent, were established by means of 1D- and 2D-NMR spectroscopy and, for 3b and 7c, also by X-Ray measurements.

Original languageEnglish
Pages (from-to)63-74
Number of pages12
JournalHeterocycles
Volume63
Issue number1
Publication statusPublished - jan. 1 2004

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Oxazines
Oxazoles
Alkanolamines
Cross-Linking Reagents
Cyclopentanes
Anhydrides
Cyclization
Toluene
Nuclear magnetic resonance spectroscopy
Magnetic Resonance Spectroscopy
X-Rays
Oxygen
Derivatives
X rays
Acids
benzimidazole
Isoindol-1-one
1,2-diaminobenzene
imidazole
oxazine 1

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Miklós, F., Kanizsai, I., Thomas, S., Kleinpeter, E., Sillanpää, R., & Stájer, G. (2004). Preparation and structure of diexo-oxanorbornane-fused 1,3-heterocycles. Heterocycles, 63(1), 63-74.

Preparation and structure of diexo-oxanorbornane-fused 1,3-heterocycles. / Miklós, Ferenc; Kanizsai, Iván; Thomas, Steffen; Kleinpeter, Erich; Sillanpää, Reijo; Stájer, Géza.

In: Heterocycles, Vol. 63, No. 1, 01.01.2004, p. 63-74.

Research output: Article

Miklós, F, Kanizsai, I, Thomas, S, Kleinpeter, E, Sillanpää, R & Stájer, G 2004, 'Preparation and structure of diexo-oxanorbornane-fused 1,3-heterocycles', Heterocycles, vol. 63, no. 1, pp. 63-74.
Miklós F, Kanizsai I, Thomas S, Kleinpeter E, Sillanpää R, Stájer G. Preparation and structure of diexo-oxanorbornane-fused 1,3-heterocycles. Heterocycles. 2004 jan. 1;63(1):63-74.
Miklós, Ferenc ; Kanizsai, Iván ; Thomas, Steffen ; Kleinpeter, Erich ; Sillanpää, Reijo ; Stájer, Géza. / Preparation and structure of diexo-oxanorbornane-fused 1,3-heterocycles. In: Heterocycles. 2004 ; Vol. 63, No. 1. pp. 63-74.
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