A Synthetic Approach to Perhydro-3-isoquinolinones Bearing an Angular Methyl Group via Organocuprate Addition

Stanetty, Peter; Bahardoust, M. Hassan; Mihovilovič, Marko D.; Mereiter, Kurt

doi:10.1007/pl00010187

Cited by 3 publications

(2 citation statements)

References 6 publications

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“…Elemental analyses were carried out in the Microanalytical Laboratory, University of Vienna. The NMR spectra were recorded from CDCl 3 solutions on a Bruker AC 200 (200 MHz) spectrometer and chemical shifts are reported in ppm using Me 4 Si as internal standard.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 9-azasteroid partial structures via Birch reduction as key step

Stanetty¹,

Kasemann²,

Mereiter³

et al. 2005

Arkivoc

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A high-energy intermediate model for the inhibition of the ergosterol biosynthesis suggests 9-azasteroids as potential antimycotics. Key step for the approach described in this work involves a Birch reduction of substituted quinoline structures. The diastereoselectivity of this reaction was studied. Subsequent functionalization to incorporate the lipophilic properties of the steroidal core afforded N-substituted perhydro-quinolinols as mimics of the AB-ring system of steroids.

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Section: Methodsmentioning

confidence: 99%

Synthesis of 9-azasteroid partial structures via Birch reduction as key step

Stanetty¹,

Kasemann²,

Mereiter³

et al. 2005

Arkivoc

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“…This gets support from the fact that the formation of cyclized product 3a did occur, albeit in low yield (29%), because the hydroxyl group is known to be a poor leaving group. Hence, we decided to improve the leaving group tendency of the hydroxyl group by derivatizing it with a tosyl group ).…”

mentioning

confidence: 99%

Unprecedented SnCl₂-Mediated Cyclization of Nitro Arenes via N−N Bond Formation

et al. 2006

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[reaction: see text] A mild, efficient, one-pot protocol for the cyclization of nitro-aryl substrates using SnCl(2) has been described. The mechanistic course of the reaction suggests the involvement of a hydroxylamine intermediate leading to an intramolecular cyclization via N-N bond formation. The versatility of the methodology has been demonstrated by using two nitro-aryl substrates derived from dihydroisoquinolines and dihydro-beta-carbolines. The intramolecular cyclization led to the formation of indazoles in high yields and purities.

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