Journal
ACS OMEGA
Volume 7, Issue 42, Pages 38045-38052Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsomega.2c05394
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Funding
- Science and Engineering Research Board (SERB) , New Delhi [CRG/2021/007367]
- University of Grants Commission (UGC) , New Delhi
- DST, New Delhi [DST-INSPIRE/03/2018/001338]
- CSIR-IICT Communication [2022/189]
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An efficient and straightforward method for the synthesis of diversified seleno-azaspiro-2,5-cyclohexadienones from N-(4-methoxy aryl)propiolamides using elemental selenium and boronic acids has been demonstrated. This method can also be extended to N-(4-methoxy aryl)propiolates and biaryl ynones to access the corresponding selenylated oxospiro-2,5-cyclohexadienones and spiro[5,5]trienones, respectively.
An efficient and straightforward synthesis of diversified seleno-azaspiro-2,5-cyclohexadienones from N-(4-me-thoxy aryl)propiolamides using elemental selenium and boronic acids has been demonstrated. The reaction proceeds through silver-catalyzed oxidative dearomatization in the presence of potassium persulfate (K2S2O8) as the oxidant. Further, this approach was extended to N-(4-methoxy aryl)propiolates and biaryl ynones to access the corresponding selenylated oxospiro-2,5-cyclohexadie-nones and spiro[5,5]trienones, respectively. The present three-component method offers the diverse substitutions on selenium involving two C-Se and one C-C bond formations.
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