- A New Ring Interconversion: 3-Azido-1,2,4-thiadiazoles from the Reaction of Thionyl Chloride with 1-Alkyl-5-aminotetrazoles
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Heating of some 1-alkyl-5-aminotetrazoles with thionyl chloride gave 3-azido-1,2,4-thiadiazoles in a reaction involving 5-N-sulphinylaminotetrazoles as intermediates.
- Butler, Richard N.,O'Donoghue, Denis A.,O'Halloran, Gerard A.
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p. 800 - 801
(2007/10/02)
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- Cyclic Meso-ionic Compounds. Part 23. Novel Chemistry of 1,2,4-Thiadiazoles and Their Transformation into Meso-ionic 1,2,4-Thiadiazolium Derivatives
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Representatives of two new classes of meso-ionic heterocycles have been synthesised, the 1,2,4-thiadiazolium-3-olate (8) and the 1,2,4-thiadiazolium-3-tosylaminide (25).The reactions of 1,2,4-thiadiazoles and nucleophiles follow two general pathways: (i) reductive transformation to N-thiobenzoyl derivatives and (ii) elimination of elemental sulphur and the formation of N-benzoyl derivatives.A mechanistic rationale is proposed for the operation of pathways (i) and (ii).Earlier views on the oxidative formation of certain 1,2,4-thiadiazoles are corrected.A novel synthetic route to heterocycles containing sulphur-nitrogen bonds is described. 1,2,4-Thiadiazoles are formed by oxidation of N-thiobezoylureas and N-thiobenzoylguanidines by bis(4-methoxyphenyl) telluroxide.
- Newton, Christopher G.,Ollis, W. David,Wright, Derek E.
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