Expeditious Access to Spiro-Fused 2,5-Cyclohexadienones <i>via</i> Thio(seleno)cyanative <i>ipso</i>-Cyclization
Chada Raji Reddy, Uprety Ajaykumar, Dattahari H. Kolgave
Abstract
A facile oxidative dearomatization of N-(p-methoxyaryl)propiolamides has been established for the synthesis of spiro-fused 2,5-cyclohexadienone frameworks via thio(seleno)cyanative ipso-cyclization in the presence of ceric ammonium nitrate (CAN) as the oxidant. The present method, involving the formation of C–S and C–C bonds, was also extended to (p-methoxyaryl)propiolates for thiocyanative ipso-cyclization. Furthermore, the obtained chalcogeno-spirocyclohexadienones were transformed into uniquely functionalized spirocyclohexadienone derivatives.
Topics & Concepts
ChemistryThio-Combinatorial chemistryMedicinal chemistryStereochemistrySulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsCatalytic C–H Functionalization Methods