Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 23, Pages 15521-15531Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02270
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Funding
- Department of Science and Technology (DST), New Delhi [DST-INSPIRE/03/2018/001338]
- University Grants Commission (UGC), New Delhi
- Council of Scientific & Industrial Research (CSIR) [IICT/Pubs./2020/278]
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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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