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Publication Details
AFRICAN RESEARCH NEXUS
SHINING A SPOTLIGHT ON AFRICAN RESEARCH
chemistry
Synthesis of unexpected bifunctionalized thiazoles by nucleophilic attack on allenyl isothiocyanate
European Journal of Organic Chemistry, Volume 2014, No. 14, Year 2014
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Description
Treatment of allenyl isothiocyanate with a variety of nucleophiles leads to 5-methylthiazoles with a functional group at the 2-position. The same pattern of reactivity is also seen with N-aminophthalimide. In the presence of azide salt, hydrazoic acid, or N,N-disubstituted hydroxylamines, however, allenyl isothiocyanate is converted into bifunctionalized thiazoles. We explain the formation of these products by nucleophilic addition at the isothiocyanato moiety followed by ring closure and an N-N or N-O cleavage reaction to generate short-lived 2-imino-5-methylidenethiazole or 5-methylidenethiazol-2-one. Such intermediates are trapped by addition reactions to give the final heterocyclic compounds. In the case of N,N-disubstituted hydroxylamines, the primary addition products with allenyl isothiocyanate can be detected as unstable intermediates by IR and NMR spectroscopy. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Authors & Co-Authors
Jawabrah Al-Hourani, Baker
Germany, Chemnitz
Technische Universität Chemnitz
Jordan, Amman
American University of Madaba
Richter, Frank
Germany, Chemnitz
Technische Universität Chemnitz
Vrobel, Kai
Germany, Chemnitz
Technische Universität Chemnitz
Banert, Klaus
Germany, Chemnitz
Technische Universität Chemnitz
Korb, Marcus
Germany, Chemnitz
Technische Universität Chemnitz
Rüffer, Tobias
Germany, Chemnitz
Technische Universität Chemnitz
Walfort, Bernhard
Germany, Chemnitz
Technische Universität Chemnitz
Lang, Heinrich J.
Germany, Chemnitz
Technische Universität Chemnitz
Statistics
Citations: 8
Authors: 8
Affiliations: 2
Identifiers
Doi:
10.1002/ejoc.201301851
ISSN:
1434193X