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The reaction of aryl acetylide anions with phenyl isocyanate and subsequent addition of a protonating agent such as ethanol affords good yields of 3-aminomaleimides, formed by the cyclization of one molecule of alkyne with two isocyanates. When the reaction is quenched with water instead, cyclopentadienone imines are formed as the major products.
The reaction of lithium phenylacetylide with phenyl isothiocyanate followed by the addition of ethanol produces a crystallographically-characterised heterocycle formed by the cyclisation of two molecules each of acetylene and isothiocyanate, and which is identical to the dimer of the acetylenic thioamide PhCCC(S)NHPh, described almost a century ago.
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