Evaluation of Electrophilic Heteroaromatic Substitution: Synthesis of Heteroaromatic-Fused Pyrimidine Derivatives via Sequential Three-Component Heterocyclization
作者： Fung Fuh Wong , Yu-Ying Huang , Chun-Hsi Chang
DOI: 10.1021/JO301463M
关键词:
摘要: A new sequential three-component heterocyclization was developed by reacting aromatic and heterocyclic substrates, including aminobenzenes, 1-aminonaphthalene, 2-aminopyrazines, 5-aminopyrazoles, 3-aminopyridine, 5-aminopyrimidine, 5-aminoquinoline, 8-aminoquinoline, with formamide in the presence of PBr3. The reaction gave corresponding pyrazolo[3,4-d]pyrimidines good yields (59–96%), except for aminobenzenes 3-aminopyridine. plausible mechanism involving amidination, electrophilic substitution imination, oxidative cyclization three steps proposed to account heterocyclization. reactivity found proportional electrophilicity or substrate.
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