Synthesis of beta-tosylethylhydrazine and its use in preparation of N-protected pyrazoles and 5-aminopyrazoles

摘要

beta-Tosylethylhydrazine (6) can be prepared efficiently in one step from commercially available p-tolyl vinyl sulfone (7) and hydrazine hydrate. This hydrazine reacts with both 1,3-diketones and conjugated ynones in glacial acetic acid to provide a variety of N-tosylethyl-protected (TSE) pyrazoles in good yields. The TSE group can be removed from the pyrazoles using potassium t-butoxide in THF at -30 degreesC-rt. In addition, hydrazine 6 condenses with beta-ketonitriles and beta-aminoacrylonitriles to afford 5-aminopyrazoles, which can be deprotected by brief treatment with NaOEt in EtOR/DMSO at 45 degreesC. (C) 2003 Elsevier Ltd. All rights reserved. [References: 22]