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Synthesis 1997; 1997(9): 1021-1026
DOI: 10.1055/s-1997-1298
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5,6-Dihydropyrrolo[1,2-c]pyrimidine-1,3(2H,5H)-diones as Annulated Analogues of the Anti-HIV Compound MKC-442 (6-Benzyl-1-(ethoxymethyl)-5-isopropyluracil)

Krzysztof Danel*
  • *Department of Chemistry, Odense University, DK-5230 Odense M, Denmark
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Publication Date:
31 December 2000 (online)

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Annulated analogues of the anti-HIV compound MKC-442 were synthesized from 6-benzoyl-5-ethyl-2,4-dimethoxypyrimidine (4) by reaction with Zn/NH4Cl and 3-bromopropene. The intermediate homoallylic alcohol is subjected to a ring closure reaction by treatment with bromine either directly or after O-benzylation to give 5,6-dihyddropyrrolo[1,2-c]pyrimidinones. No activity against HIV was observed, neither for the annulated analogues nor the derivatives synthesized from 4. Only compound 4 showed activity against HIV-1.

cyclization by bromoalkylation

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