Abstract
1,2,3,4-Tetrahydroisoquinoline-1-carbonitriles can serve as starting materials for the one-pot synthesis of 5,6-dihydropyrrolo[2,1 a]isoquinolines and 1-benzyl-3,4-dihydroisoquinolines. The latter compounds were transformed to lamellarin G trimethyl ether and lamellarin U in short reaction sequences. This method allows the introduction of acid-sensitive protecting groups for the phenolic hydroxy functions which would be cleaved under the harsh conditions of the classical Bischler-Napieralski reaction.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkylation
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Coumarins / chemical synthesis*
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Coumarins / chemistry
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Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
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Heterocyclic Compounds, 4 or More Rings / chemistry
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Isoquinolines / chemical synthesis*
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Isoquinolines / chemistry
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Magnetic Resonance Spectroscopy
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Mass Spectrometry
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Nitriles / chemistry*
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Spectrophotometry, Infrared
Substances
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Coumarins
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Heterocyclic Compounds, 4 or More Rings
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Isoquinolines
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Nitriles
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lamellarin G trimethyl ether