Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 14, Pages 8780-8791Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c00275
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Funding
- Science & Engineering Research Board (SERB), Department of Science and Technology (DST), India [EMR/2017/002601]
- CSIR
- CSIR-IICT [IICT/Pubs./2020/022]
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A copper-catalyzed tandem process integrating regioselective N-arylation, followed by aza-Michael addition, is disclosed using 2-aminobenzothiazoles and ortho-halo cinnamic acid congeners. This process generated diverse tetracyclic 5H-benzothiazolo[3,2-a]quinazoline derivatives in moderate to good yields. The present tandem reaction appears to proceed through concomitant ring opening of 2-aminobenzothiazole and S-arylation to give the ortho-cyanamide-substituted diary! thioether intermediate. The thus generated intermediate likely undergoes an unprecedented Truce-Smiles-type rearrangement involving S- to N-aryl migration, followed by reformation of the thiazole ring and intramolecular aza-Michael addition to furnish the title products.
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