Isonitrile Trapping Reactions under Thermolysis of Alkoxyamines for the Synthesis of Quinolines
2006; American Chemical Society; Volume: 8; Issue: 9 Linguagem: Inglês
10.1021/ol0604421
ISSN1523-7060
Autores Tópico(s)Radical Photochemical Reactions
Resumo[reaction: see text] An efficient tandem radical process comprising a thermal alkoxyamine homolysis, an isonitrile trapping reaction, a 5-exo-trig cyclization, and a homolytic aromatic substitution leads to substituted dihydroquinolines. Depending on the substituent R(1), oxidation to dihydro-1H-cyclopenta[b]quinolines (for R(1) = aryl) or tautomerization to tetrahydro-1H-cyclopenta[b]quinolines (for R(1) = CO(2)Me, CN) occurs. The heterocycles are obtained in moderate to good yields. Upon using microwave-induced heating, the reaction time can be shortened from 3 days to 30 min.
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