The Synthesis of 1,3,4-Oxadiazolo[3,2-<I>b</I>]isoquinoline and 1,3,4-Thiadiazolo-[3,2-<I>b</I>]isoquinoline Derivatives from Homophthalic Anhydride
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The synthesis of 1,3,4-oxadiazolo[3,2-<I>b</I>]isoquinoline and 1,3,4-thiadiazolo[3,2-<I>b</I>]isoquinoline derivatives is described. The reaction of homophthalic anhydride (<B>1</B>) with acylhydrazines (<B>2</B>) afforded 2-acylamino-1,2,3,4-tetrahydroisoquinoline-1,3-diones (<B>3</B>) or 1-(<I>o</I>-carboxyphenylacetyl)-2-acylhydrazines (<B>4</B>). The treatment of <B>3</B> or <B>4</B> with polyphosphoric acid gave 2-substituted 1,3,4-oxadiazolo[3,2-<I>b</I>]isoquinolin-5(5<I>H</I>)-ones (<B>5</B>) in quantitative yields. The treatment of <B>3</B> or <B>4</B> with phosphorus pentasulfide gave 2-substituted 1,3,4-thiadiazolo[3,2-<I>b</I>]-isoquinoline-5(5<I>H</I>)-thiones (<B>6</B>). 2-Phenyl-1,3,4-oxadiazolo[3,2-<I>b</I>]isoquinoline-5(5<I>H</I>)-thione (<B>9</B>) was obtained by the reaction of <B>5a</B> with phosphorus pentasulfide.
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- The Synthesis of 1,3,4-Oxadiazolo[3,2-b]isoquinoline and 1,3,4-Thiadiazolo-[3,2-b]isoquinoline Derivatives from Homophthalic Anhydride