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Moody CJ, Slawin AM, Willows D. Dirhodium(II) tetraacetate catalysed reactions of diazo thioamides: isolation and cycloaddition of anhydro-4-hydroxy-1,3-thiazolium hydroxides (thioisomünchnones), an approach to analogues of dehydrogliotoxin. Org Biomol Chem. 2003;1(15):2716-22doi: 10.1039/b305698h.
Moody, C. J., Slawin, A. M., & Willows, D. (2003). Dirhodium(II) tetraacetate catalysed reactions of diazo thioamides: isolation and cycloaddition of anhydro-4-hydroxy-1,3-thiazolium hydroxides (thioisomünchnones), an approach to analogues of dehydrogliotoxin. Organic & biomolecular chemistry, 1(15), 2716-22. https://doi.org/10.1039/b305698h
Moody, Christopher J, et al. "Dirhodium(II) tetraacetate catalysed reactions of diazo thioamides: isolation and cycloaddition of anhydro-4-hydroxy-1,3-thiazolium hydroxides (thioisomünchnones), an approach to analogues of dehydrogliotoxin." Organic & biomolecular chemistry vol. 1,15 (2003): 2716-22. doi: https://doi.org/10.1039/b305698h
Moody CJ, Slawin AM, Willows D. Dirhodium(II) tetraacetate catalysed reactions of diazo thioamides: isolation and cycloaddition of anhydro-4-hydroxy-1,3-thiazolium hydroxides (thioisomünchnones), an approach to analogues of dehydrogliotoxin. Org Biomol Chem. 2003 Aug 07;1(15):2716-22. doi: 10.1039/b305698h. PMID: 12948196.
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Org Biomol Chem. 2003 Aug 07;1(15):2716-22. doi: 10.1039/b305698h.

Dirhodium(II) tetraacetate catalysed reactions of diazo thioamides: isolation and cycloaddition of anhydro-4-hydroxy-1,3-thiazolium hydroxides (thioisomünchnones), an approach to analogues of dehydrogliotoxin.

Organic & biomolecular chemistry

Christopher J Moody, Alexandra M Z Slawin, David Willows

Affiliations

  1. School of Chemistry, University of Exeter, Stocker Road, Exeter, UK EX4 4QD. [email protected]

PMID: 12948196 DOI: 10.1039/b305698h

Abstract

Dirhodium(II) tetraacetate catalysed reaction of the indoline diazo thioamide 8 gives the thioisomünchnone 9, a stable characterisable solid. This masked thiocarbonyl ylide undergoes 1,3-dipolar cycloaddition with N-methylmaleimide and maleic anhydride to give the exo-cycloadducts 10 and 11, characterised by X-ray crystallography. The thioisomünchnone 18, derived from diazo thioamide 17, is an extremely stable crystalline mesoionic system which can be characterised by X-ray crystallography but fails to undergo intramolecular cycloaddition. The related thioisomünchnone 19 can be generated by reaction of indoline-2-thione 7 with bromoacetyl chloride in the presence of triethylamine, and undergoes cycloaddition to give adducts 20 and 21.

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