Preparation of 5-Aryl-2-Alkyltetrazoles with Aromatic Aldehydes, Alkylhydrazine, Di-tert-butyl Azodicarboxylate, and [Bis(trifluoroacetoxy)iodo]benzene
A variety of 5-aryl-2-methyltetrazoles and 5-aryl-2-benzyltetrazoles were directly prepared in good to moderate yields by the reaction of aromatic aldehydes with methylhydrazine and benzylhydrazine, followed by treatment with di-tert-butyl azodicarboxylate and [bis(trifluoroacetoxy)iodo]benzene in a mixture of dichloromethane and 2,2,2-trifluoroethanol at room temperature. The present method is a novel one-pot preparation of 5-aryl-2-methyltetrazoles and 5-aryl-2-benzyltetrazoles through a [2N + 2N] combination under transition metal-free and mild conditions.
N-silyloxaziridines: Synthesis and use for electrophilic amination
N-Silyloxaziridines were synthesized for the first time. Their tert-butyldiphenylsilyl (TBDPS) derivatives were stable reagents that were prepared on a multigram scale in three steps and in 44% overall yield from the corresponding benzylamines. They were mild electrophilic aminating reagents that reacted at room temperature with diversely substituted primary and secondary amines to produce N-monoalkyl or N,N-dialkyl benzaldehyde hydrazones in 44a-87% yield.
Richy, Nicolas,Ghoraf, Mohammed,Vidal, Jo?lle
p. 10972 - 10977
(2013/02/22)
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