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Synthesis 2010(13): 2278-2286  
DOI: 10.1055/s-0029-1218794
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Preparation and N-Alkylation of 4-Aryl-1,2,4-triazoles

Stefanie C. Holm, Alexander F. Siegle, Christian Loos, Frank Rominger, Bernd F. Straub*
Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
e-Mail: straub@oci.uni-heidelberg.de;
Further Information

Publication History

Received 13 April 2010
Publication Date:
20 May 2010 (online)

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Abstract

Heating of N,N-dimethylformamide azine dihydrochloride {N′-[(dimethylamino)methylene]-N,N-dimethylhydrazonoform­amide dihydrochloride} with anilines in the absence of a solvent gave a range of 4-aryl-1,2,4-triazoles by direct transamination. Ortho-substituents were tolerated. Some triazoles were converted into symmetrically and nonsymmetrically substituted bistriazolium salts, one of which was converted into a dicopper complex.

Key words

aminations - cyclizations - heterocycles - alkylations - triazoles

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