Parallel solid-phase syntheses of 1,3,4-thiadiazolium-2-aminides

Joseph C. Kappel, T. Scott Yokum, George Barany

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

An efficient and advantageous solid-phase strategy has been developed to synthesize 1,3,4-thiadiazolium-2-aminides. The title compounds were prepared in parallel fashion according to the following compact route: (i) anchoring of aromatic aldehydes to the solid support; (ii) solution preparation of 1,4-disubstituted thiosemicarbazides from hydrazines plus isothiocyanates; (iii) trimethylsilyl chloride-promoted cyclization between the resin-bound aldehydes and 1,4-disubstituted thiosemicarbazides; and (iv) removal of the products from the solid support by acid treatment. The products (17 made in all) were cleaved with high initial purities (90-98%) and obtained in generally good isolated yields (53-94%, with one exception).

Original languageEnglish (US)
Pages (from-to)746-752
Number of pages7
JournalJournal of Combinatorial Chemistry
Volume6
Issue number5
DOIs
StatePublished - Sep 1 2004

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