Synthesis and Application of Iso(thio)cyanate‐Functionalized Calix[4]arenes

Abstract

Abstract Aminocalix[4]arenes 7–12 react with triphosgene and thiophosgene to the corresponding iso(thio)cyanate‐functionalized calix[4]arenes 13–20 . Carbamate‐ ( 21–25 ) and ureasubstituted calix[4]arenes ( 26,27 ) can be obtained via isocyanatocalix[4]arenes using a one‐pot synthesis starting from the corresponding aminocalix[4]arenes in moderate to good yields. Isothiocyanate‐functionalized calix[4]arenes 16, 18 react selectively with amines to the corresponding thioureas 28–31 in 59–83% yield. Reaction of isothiocyanate‐functionalized calix[4]arenes 16, 19, 20 with cavitands 34, 38 gives 2:2 products 42–45 in 35–42% yield.