Tetrahedron Letters p. 9407 - 9411 (2000)
Update date:2022-07-29
Topics:
Le
Rees
Sivadasan
5-Substituted tetrazoles react rapidly with Appel salt 1 at room temperature to give hydrazonoyl chlorides (14) in high yield. 5-Aminotetrazole reacts further to give an extended bis-imine (6) which, with triphenylphosphine at room temperature, rapidly gives 1,3,4-thiadiazoles 15 and 17. The mono-imines 14 react similarly to give simpler thiadiazoles 18 in high yield. By repetition of the tetrazole formation and Appel salt-triphenylphosphine sequence, these 2-cyanothiadiazoles 18 are converted in high yield into thiadiazole dimers and trimers 21, n = 1 and 2. These reactions are explained mechanistically. (C) 2000 Elsevier Science Ltd.
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