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2004
Fused pyrimidine derivatives
R 0515
Reaction of Bromomethylazoles and Tosylmethyl Isocyanide. A Novel HeterocyMethod for the Synthesis of the Core of Marine Alkaloids Variolins and
46- 152 clization
Related Azolopyrimidines. — Treatment of various N-alkoxycarbonyl protected bromomethylazoles with TosMIC (V) under phase-transfer conditions results in unprecedented formation of fused pyrimidines. The pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine
system, the heterocyclic core of the variolin family, is also available using this method
[cf. (Xa,b)]. The resulting products smoothly undergo hydrolysis, decarboxylation, and
functionalization at C-5. Attempted functionalization at C-9 gives only dimers. —
(MENDIOLA, J.; BAEZA, A.; ALVAREZ-BUILLA, J.; VAQUERO*, J. J.; J. Org.
Chem. 69 (2004) 15, 4974-4983; Dep. Quim. Org., Univ. Alcala, E-28871 Alcala de
Henares, Madrid, Spain; Eng.) — Jannicke
2004
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