This study examined the effectiveness of solventless methods in the synthesis of compounds with potentially useful medicinal and structural properties.  In the medicinal area, the syntheses of prospective inhibitors of aldosterone synthase were attempted through various condensation reactions, including aldol condensations and imine formation. Aldosterone invokes sodium reabsorption; the overproduction of which can lead to congenital heart failure and myocardial fibrosis. An absence of solvent in this case did not prove to be particularly effective, so methods involving the use of low risk solvents were implemented in reactions between various imines and aldehyde compounds, as well as reactions between various imine and aldol compounds.   In the structural area, the solventless Diels-Alder cycloaddition method was employed to successfully yield four novel bicyclo[4.3.0]non-3-ene-7,9-diones in moderate to high yield with experimental atom economies ranging from 21 to 32%, and E-factors ranged from 2.7 to 3.7.

Effectiveness of solventless condensation and Diels-Alder methods in the synthesis of prospective aldosterone synthase inhibitors and four novel bicyclo[4.3.0]non-3-ene-7,9-diones: Applications in the fields of medicinal and structural chemistry

239th National Meeting (2010)

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