ISSN:
0018-019X
Schlagwort(e):
Chemistry
;
Organic Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
Synthesis and Reactivity of Lumazine-7-sulfenic AcidsThe chemical synthesis of the pteridine-7-sulfenic acids 13-16 is described (Scheme 1). The 1,2,3,4-tetrahydro-1,3,6-trimethyl-2,4-dioxopteridine-7-sulfenic acid (14) was isolated as a stable crystalline solid. Its chemical reactivity was investigated and the physical properties determined. In the solid state, the S-oxide form 14A predominates, but in protic solvents the S-OH tautomer 14 exists most likely. In basic medium, the pteridine-7-sulfenate species is stable, whereas a low pH gives rise to a disproportionation to the disulfide 10 and the corresponding pteridine-7-sulfinic acid 37 (Scheme 4). Reaction of 14 with ethyl propiolate leads, under cis-addition, to 36, oxidation with KMnO4 forms 1,2,3,4-tetrahydro-1,3,6-trimethyl-2,4-dioxopteridine-7-sulfonic acid (38) and NaBH4 reduction the corresponding 7-mercaptopteridine dione 18 (Scheme 4).
Zusätzliches Material:
2 Ill.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/hlca.19860690517
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