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Issue 24, 2001
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The synthesis of pyrano[2,3-b]quinoxalines related to molybdopterin

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Abstract

Two cobalt complexes, 5 and 7, both containing 11,11a-dihydropyrano[2,3-b]quinoxaline nuclei, were synthesised as model substances for the molybdenum cofactor of the oxomolybdoenzymes. The organic proligands for the ene-1,2-dithiolates, from which these complexes were formed, were 1,3-dithiol-2-ones, the dianionic ligands being liberated by reaction with caesium hydroxide. The pyran ring in the tetracyclic 1,3-dithiol-2-one proligands, 4b and 6, was formed by ring closure of the side-chain alcohol in a 4-(1-hydroxyalkyl)-5-(quinoxalin-2-yl)-1,3-dithiol-2-one onto an aromatic quinoxaline via reaction with a chloroformate, generating 6-alkyloxycarbonyl-2-oxo-5a,6-dihydro-4H-[1,3]dithiolo[4′,5′:4,5]pyrano[2,3-b]quinoxalines which were then reduced with cyanoborohydride to give 6-alkyloxycarbonyl-5a,6,11,11a-tetrahydro-2-oxo-4H-[1,3]dithiolo[4′,5′:4,5]pyrano[2,3-b]quinoxalines – the proligands.

Graphical abstract: The synthesis of pyrano[2,3-b]quinoxalines related to molybdopterin

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Publication details

The article was received on 20 Sep 2001, accepted on 26 Oct 2001 and first published on 16 Nov 2001


Article type: Paper
DOI: 10.1039/B108576J
J. Chem. Soc., Perkin Trans. 1, 2001, 3232-3238

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    The synthesis of pyrano[2,3-b]quinoxalines related to molybdopterin

    B. Bradshaw, A. Dinsmore, D. Collison, C. D. Garner and J. A. Joule, J. Chem. Soc., Perkin Trans. 1, 2001, 3232
    DOI: 10.1039/B108576J

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