Abstract
Hexahydrobenzo[de]isochromanes and hexahydropyrano[3,4,5-ij]isoquinolines can be efficiently synthesized via Friedel Crafts and oxa Pictet-Spengler reaction of acrylyl enol ethers mediated by triflic acid in good yields. The reaction is highly stereoselective. Two of the hexahydrobenzo[de]isochromanes are found to have moderate antileishmanial activity.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetates / chemical synthesis
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Acetates / chemistry
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Acetates / pharmacology*
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Antiprotozoal Agents / chemical synthesis*
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Antiprotozoal Agents / chemistry
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Antiprotozoal Agents / pharmacology*
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Benzopyrans / chemical synthesis
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Benzopyrans / chemistry
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Benzopyrans / pharmacology*
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Dose-Response Relationship, Drug
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Leishmania donovani / drug effects*
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Molecular Structure
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Parasitic Sensitivity Tests
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Stereoisomerism
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Structure-Activity Relationship
Substances
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Acetates
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Antiprotozoal Agents
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Benzopyrans
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ethyl 2-(3-(4-methoxyphenyl)-3a,6,6-trimethyl-1,3,3a,4,5,6-hexahydro-benzo(de)isochroman-1-yl)acetate
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ethyl 2-(8-bromo-6,6-dimethyl-1,3,3a,4,5,6-hexahydrobenzo(de)isochroman-1-yl)acetate