Base-catalyzed condensations of ο-phthalaldehyde and thiourea
Brookbank, Carol A.
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It has been known for many years that o-phthalaldehyde undergoes ring formation reactions forming phtha1imidines. Since 1959 several dihydroxyisoindolines have been synthesized from o-phthalaldehyde and various amides. When urea was used as the amide, a 2:1 adduct of o-phthalaldehyde to urea was formed due to the two reactive amino groups in urea. This research investigated the reactions of o-phthalaldehyde with thiourea, a thioamide, as the amide. Evidence supporting the proposed structures for the products is given. This evidence is based mainly on infrared and nuclear magnetic resonance spectra, and elemental analyses. A comparison of this thiourea-o-phthalaldehyde system to the urea-o-phthalaldehyde system is discussed along with a mechanism by which these products may have been formed.