Journal
MONATSHEFTE FUR CHEMIE
Volume 138, Issue 8, Pages 771-776Publisher
SPRINGER WIEN
DOI: 10.1007/s00706-007-0665-7
Keywords
environmentally benign; ball-milling; thiazole; solid-state reactions; gas-solid diazotization
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Solid-state techniques allow for waste-free quantitative syntheses. The solid-solid reactions of alpha-haloketones with several pyrazolones and with thiosemicarbazones were shown to afford the corresponding pyrazolyl ethers and 4-substituted 2-(arylidenehydrazino)thiazoles. The product yields are quantitative in all cases and the products do not require purifying workup. Therefore, these reactions are truly solvent-free, sustainable, and no wastes are produced. A diazonium nitrate is quantitatively accessible by gas-solid reaction of the corresponding amine with NO2 gas. It is a useful material for environmental synthesis of azo dyes through solid-state coupling with a variety of coupling compounds, as e.g. beta-naphthol, acetoacetanilide, pyrazolones, and barbituric acid.
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