Diels-Alder Reaction of Pyrano[3,4-b]indolones with Electron-Poor Pyridazinones: a New Pathway to Carbazole-Fused Pyridazines

Norbert Haider, Johann Käferböck, and Péter Mátyus

Spectra of Compounds 3a,b, 5a,b, 6, and 7:

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CompoundStructureSpectrum
3a NMR
IR
MS
3b NMR
IR
MS
5a NMR
IR
MS
5b NMR
IR
MS
6 NMR
IR
MS
7 NMR
IR
MS

Selected NOE Difference Spectra:

NOE spectrum #1, compound 3a
upper trace: 300 MHz 1H-NMR spectrum of 3a (d6-DMSO)
lower trace: NOE difference spectrum of 3a; irradiation of CH3-5 (2.78 ppm)

NOE spectrum #2, compound 3a
upper trace: 300 MHz 1H-NMR spectrum of 3a (d6-DMSO)
lower trace: NOE difference spectrum of 3a; irradiation of CH3-11 (3.46 ppm)

NOE spectrum, compound 7
upper trace: downfield region of the 300 MHz 1H-NMR spectrum of 7 (d6-DMSO)
lower trace: NOE difference spectrum of 7; irradiation of H-11: positive effects for H-10 and H-12, negative effect for H-9
("three-spin effect" [cf. D. Neuhaus and M. Williamson, 'The Nuclear Overhauser Effect in Structural and Conformational Analysis', VCH, New York - Weinheim - Cambridge, 1988, p. 81.])

NH, 15 June 1998