Solvent-controlled regioselective C(5)–H/N(1)–H bond alkylations of indolines and C(6)–H bond alkylations of 1,2,3,4-tetrahydroquinolines with <i>para</i>-quinone methides
Volkan Akyildiz, Ferruh Lafzi, Haydar Kilic, Nurullah Saraçoğlu
Abstract
Solvent-switched regioselective N -alkylations (in HFIP : DCM) and C5-alkylations (in HFIP) of indolines using a broad range of p -QMs have been developed. The protocol successfully worked for the C6-alkylations of 1,2,3,4-tetrahydroquinolines.
Topics & Concepts
ChemistryIndolineAlkylationNucleophileRegioselectivityIndole testMedicinal chemistrySolventCatalysisOrganic chemistrySynthesis of Indole DerivativesAxial and Atropisomeric Chirality SynthesisSulfur-Based Synthesis Techniques