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Expeditious Access to Spiro-Fused 2,5-Cyclohexadienones via Thio(seleno)cyanative ipso-Cyclization

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journal contribution
posted on 23.11.2020, 06:49 by Chada Raji Reddy, Uprety Ajaykumar, Dattahari H. Kolgave
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.