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Synthesis 2000; 2000(11): 1591-1597
DOI: 10.1055/s-2000-7600
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Synthesis of Hydrazines with Aromatic Substituents Using Triarylbismuth Reagents

Olavi Loog* , Uno Mäeorg, Ulf Ragnarsson
  • *Department of Biochemistry, University of Uppsala, Biomedial Center, PO Box 576, SE-751 23 Uppsala, Sweden; Fax + 46 (18) 55 21 39; E-mail: urbki@bmc.uu.se
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Publication Date:
31 December 2000 (online)

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Smooth monoarylation of two triprotected hydrazine reagents under mild conditions has been accomplished using triarylbismuthanes in the presence of copper acetate and amine to give products 3 and 6 in excellent yield. Arylation on N 2 after selective deprotection of derivatives with alkyl or aryl substituents on N 1, resulting in compounds 8 and 9, is also demonstrated. Furthermore, other products derived from these reagents with free N-alkyl and N-aryl functions undergo the same reaction to give substances such as 10 and 11. As a result, the scope of the original hydrazine reagents has been further extended. A few reference compounds have also been prepared directly from phenylhydrazine.

N-arylations - arylbismuthanes - multisubstituted hydrazines - organometallic reagents - stepwise synthesis

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