Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 15, Pages 6596-6608Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01242
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Funding
- UGC, New Delhi, India
- CSIR, New Delhi, India
- CSIR network project [CSC 0108]
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An efficient synthesis of 2-(alpha-styryl)-2,3-dihydroquinazolin-4-ones and 3-(alpha-styryl)-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxides has been achieved in 39-94% yield through palladium-catalyzed cyclocondensation of aryl/vinyl iodides with allenamides 13-15 and 22, respectively. Base treatment of the N-tosylated products provides an easy access to 2-(astyryl)quinazolin-4(3H)-ones and 3-(alpha-styryl)-1,2,4-benzothiadiazine-1,1-dioxides, hitherto unknown heterocycles. The method has been tested with phenyl substituted allenamides, applied for bis-heteroannulation, and used in the preparation of analogues of the natural product Luotonin F.
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