Pteridines, XCIII. Reactions of 6-Chloro-, 7 -Chloro- and 6,7-Dichloro-1,3-dimethyllumazines with N-Nucleophiles

~~~ ~Pteridines: Synthesis and Characteristics of 5,6-Dihydro-6-( 1,2,3-trihydroxypropyl)pteridines: Covalent Intramolecular AdductsVarious 5,6-diaminopyrimidines (1, 15, 24, 33) were condensed with the phenylhydrazones of ~-( 2 ) and D-arabinoSe (3) in acidic medium under N, to give formal 5,6-dihydro-6-( 1,2,3-trihydroxypropyl)pteridines (see, e.g., 4 and 5), the latter turned out to exist prcferentially as intramolecular adducts, the hexahydropyrano-[3,2-g]pteridines 6, 7, 16, 17, 25, 26, and 34, formed subsequently by addition of the terminal OH group of the side-chain to the C(7)=N(8) bond of the pteridine moiety. Spectroscopically, the isomeric hexahydrofuro-[3,2-g]pteridines 10,11,18, 19, and 35 were also detected as minor components in the equilibrium mixtures. In the 4-amino-2-(methylthio)pteridine series, crystallization of 6 and 7 led to the stereochemically pure (3S,4R,4aR,10aS)-6-amino-3,4,4a,5,l0,l0a-hexahydro-~-(methylthio)-2~-pyrano[3,2-g]pteridine-3,4-diol (8) and its corresponding enantiomer 9, respectively. Structure 8 was proven by X-ray analysis. Acylation of the hexahydropyrano[3,2-g]pteridines yielded the more Stable tri-, tetra-, and pentaacetyl derivatives 12-14, 2&23, 27-32, and 37-39 which were characterized and of which the absolute and relative configurations were determined ('H-and I3C-NMR and UV spectra, chiroptical measurements, elemental analyses).

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Bicyclic 6-6 Systems: Pteridines

Pfleiderer

1996

Comprehensive Heterocyclic Chemistry II

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Pteridines, XCIII. Reactions of 6-Chloro-, 7 -Chloro- and 6,7-Dichloro-1,3-dimethyllumazines with N-Nucleophiles

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ChemInform Abstract: Pteridines. Part 93. Reactions of 6‐Chloro‐ (VI), (VIII), 7‐Chloro‐(I), and 6,7‐Dichloro‐1,3‐dimethyllumazines (IV) with N‐Nucleophiles.

ChemInform Abstract: Pteridines. Part 93. Reactions of 6‐Chloro‐ (VI), (VIII), 7‐Chloro‐(I), and 6,7‐Dichloro‐1,3‐dimethyllumazines (IV) with N‐Nucleophiles.

Pteridine. Teil XCIV. Synthese und Eigenschaften von 5,6‐Dihydro‐6‐(1,2,3‐trihydroxypropyl)pteridinen: Kovalente intramolekulare Addukte

Bicyclic 6-6 Systems: Pteridines

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