Metal-free visible-light induced cyclization/substitution cascade reaction of alkyne-tethered cyclohexadienones and diselenides: access to 5-hydroxy-3-selenyl-4a,8a-dihydro-2-chromen-6(5)-ones

A simple and efficient Se-radical triggered cyclization/substitution cascade reaction of alkyne-tethered cyclohexadienones to afford 5-hydroxy-3-selenyl-4a,8a-dihydro-2 H -chromen-6(5 H )-ones has been developed. This transformation via the 3,5-diselenyl-4a,8a-dihydro-2 H -chromen-6(5 H )-one interm...

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Published inGreen chemistry : an international journal and green chemistry resource : GC Vol. 21; no. 13; pp. 3547 - 3551
Main Authors Ma, Xian-Li, Wang, Qian, Feng, Xi-Yuan, Mo, Zu-Yu, Pan, Ying-Ming, Chen, Yan-Yan, Xin, Mao, Xu, Yan-Li
Format Journal Article
Published 01.07.2019
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Summary:A simple and efficient Se-radical triggered cyclization/substitution cascade reaction of alkyne-tethered cyclohexadienones to afford 5-hydroxy-3-selenyl-4a,8a-dihydro-2 H -chromen-6(5 H )-ones has been developed. This transformation via the 3,5-diselenyl-4a,8a-dihydro-2 H -chromen-6(5 H )-one intermediate followed by hydrolysis in the presence of CsOAc affords the desired product 3 . The resulting products were tested for their in vitro anticancer activity using MTT assay, and compounds 3e and 3q showed potent cancer cell-growth inhibition activities. A simple and efficient Se-radical triggered cyclization/substitution cascade reaction of alkyne-tethered cyclohexadienones to the product of 3 has been developed. The compounds 3e and 3q showed potent cancer cell-growth inhibition activities.
Bibliography:Electronic supplementary information (ESI) available. CCDC
For ESI and crystallographic data in CIF or other electronic format see DOI
10.1039/c9gc00570f
and
1886767
1886766
ISSN:1463-9262
1463-9270
DOI:10.1039/c9gc00570f