Isonitrile trapping reactions under thermolysis of alkoxyamines for the synthesis of quinolines.
[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.
Janza
Birgit
B
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster, Germany.
Studer
Armido
A