Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 4, Pages 2173-2181Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b03092
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Funding
- Science and Engineering Research Board, New Delhi [SERB/EMR/2015/002482]
- Council of Scientific and Industrial Research, New Delhi, India [02(0263)/16/EMR-II]
- CSIR
- UGC, New Delhi
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A facile, cost-effective, and highly efficient copper-catalyzed, TEMPO-mediated straightforward synthesis of 2,3-disubstituted naphtho[2,1-b]thiophene-4,5-diones has been achieved via cross-dehydrogenative thienannulation. The reaction proceeded via in situ generated naphthalene-1,2-diones by dearomatization of beta-naphthols, followed by oxidative heteroannulation with alpha-enolic dithioesters chemoselectively in an open flask. Further, the naphtho[2,1-b]thiophene-4,5-diones undergo L-proline-catalyzed cross-dehydrative coupling with ortho-phenylenediamine enabling pentacyclic benzo[a]thieno[3,2-c]phenazines in good yields under solvent-free conditions. A mechanistic rationale for this cascade reaction sequence is well supported by the control experiments.
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