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. 2020 Dec 4;85(23):15521-15531.
doi: 10.1021/acs.joc.0c02270. Epub 2020 Nov 22.

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

Chada Raji Reddy  1   2 , Uprety Ajaykumar  1   2 , Dattahari H Kolgave  1   2
Affiliations

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

Chada Raji Reddy et al. J Org Chem. .

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.

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