Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 24, Pages 8522-8532Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo101902z
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Funding
- National Natural Science Foundation of China [20872074, 21072110]
- Natural Science Foundation of Shandong Province [Z2008B03, ZR2010BM007]
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Regioselective synthesis of functionalized tetrahydrobenzo[b]pyrans has been developed by multi-component reactions (MCRs) and tandem [3 + 3] annulations of beta-benzoylthioacetanilides or beta-(2-haloaroyl)thioacetanilides as valuable sources with aromatic aldehydes and 5,5-dimethy1-1,3-cyclohexanedione catalyzed by triethylamine. This MCR followed by a postcondensation cyclization via an intramolecular SNAr in the presence of K2CO3 led to an unprecedented novel chromeno-[2,3-b]quinoline framework containing an important chromene moiety in good yields. The reactions were very mild, convenient, and o-selective to form new fused tetracyclic target molecules.
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