Cycloadditions of isoquinolinium salts: A new route to benz(cd);indoles.
Item
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Title
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Cycloadditions of isoquinolinium salts: A new route to benz(cd);indoles.
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Identifier
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AAI9119681
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identifier
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9119681
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Creator
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Soll, Clifford E.
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Contributor
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Adviser: Richard W. Franck
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Date
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1991
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Language
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English
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Publisher
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City University of New York.
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Subject
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Chemistry, Organic
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Abstract
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The Bradsher cycloaddition of isoquinolinium salts involving isoquinolines substituted at the 5-position with nitrogen were investigated as a new route to benz(cd) indoles. Upon ring opening of the initial tricyclic adducts, the 5-position nitrogen interacts with the aldehyde generated to construct the basic carbocyclic skeleton of this ring system. Dehydration followed by functional group interconversions led to the synthesis of Uhle's Ketone, a known precursor to the ergot alkaloid framework.;This type of cycloaddition using methoxycyclohexene was used to construct the carbon skeleton of the hapalindoles. These are a class of compounds, extracted from the blue-green alga, Hapalosiphon Fontanalis that exhibit antibacterial and antimycotic activity.;During the course of our work we developed a new method for the dedinitrophenylation of our ring opened cycloadducts. This reaction using aqueous lithium borohydride was investigated as a general procedure for the deprotection of 2,4-dinitrophenylamines.
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Type
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dissertation
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Source
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PQT Legacy CUNY.xlsx
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degree
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Ph.D.
