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Synfacts 2005(1): 0171-0171  
DOI: 10.1055/s-2005-916004
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Solid Phase Synthesis of Small Heterocyclic Scaffolds

Contributor(s): Yasuhiro Uozumi, Maki Minakawa
R. Severinsen, J. P. Kilburn, J. F. Lau*
Medicinal Chemistry Research, Novo Nordisk A/S, Denmark
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Publikationsverlauf

Publikationsdatum:
21. September 2005 (online)

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Significance

2,5-Disubstituted [1,3,4]-thiadiazoles and [1,3,4]-oxadiazoles were prepared via several steps starting with thiosemicarbazide 1 or semicarbazide 2 anchored on the commercially available [2-(3,5-dimethoxy-4-formylphenoxy)ethoxy]methyl polystyrene. 5-Alkylthio-2-alkyl­amino-[1,3,4]-thiadiazoles 3a (14 variations, 45-82% yield), 5-alkyl-2-alkylamino-[1,3,4]-thia­diazoles 3b (12 variations, 47-76% yield), 5-acyl­amino-2-alkylamino-[1,3,4]-thiadiazoles 3c (23 variations, 31-86% yield) and 2,5-bis(alkylamino)-[1,3,4]-oxadiazoles 3d (13 variations, 58-89% yield) were readily isolated after TFA-mediated cleavage from the corresponding resin beads.