Rh(III)-catalyzed ortho C-H activation/olefination of phenol carbamates has been developed. High regioselectivity is observed with a range of phenol carbamates enabling efficient coupling with acrylates and styrenes. This reaction exhibits different reactivity as compared to the Pd-catalyzed ortho-arylation reaction of phenol esters and provides a new approach for the synthesis of ortho-substituted phenols.
The carbodiimides 4, obtained from an aza-Wittig reactions of iminophosphorane 3 with aromatic isocyanates, reacted with primary amines in the presence of catalytic amounts of sodium alkoxide to give selectively 2-alkylamino-3-aryl-6-(1H-1,2,4-triazol-1-yl)-thieno[2,3-d]-pyrimidin-4(3H)-ones 6 in good yields. Compounds 6 exhibit fungicidal activity; e.g., compound 6h showing the best inhibitive activity (92%) against Colletotrichum gossypii in 50 mg/L.
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