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Paper | Regular issue | Vol 68, No. 10, 2006, pp.2113-2122
Published online, 11th August, 2006
DOI: 10.3987/COM-06-10836
Phenylcarbamoylation of N-Acetyl-1,2,4-triazolium-4-aminides Revisited

Dietrich Moderhack* and Matthias Noreiks

*Institute of Pharmaceutical Chemistry, Technical University, D-38106 Braunschweig, Germany

Abstract

The reaction of N-acetyl-1,2,4-triazolium-4-aminides (I, i.e. 1Aa-d) with phenyl isocyanate affords ring functionalized products (4a-d) rather than linear adducts (II). Analogous compounds are obtained from the triazolium-1-aminide (1Ae) and the imidazolium congener (1Af). Twofold carbamoylation to give products of type (8) occurs on reaction of aminotriazolium salts (7A) in the presence of base. Azoliums having methyl at C(5) / (2) are inert throughout (B series).