期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 82, 期 5, 页码 2355-2363出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b02693
关键词
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资金
- Department of Science & Technology (DST, New Delhi)
- J. C. Bose fellowship [SR/S2/JCB-53/2010]
- CSIR (New Delhi)
An efficient Rh(III)-catalyzed ortho-alkylation of phenoxy substrates with diazo compounds has been achieved for the first time using pyrimidine or pyridine as the directing group. Furthermore, bis-alkylation has also been achieved using parasubstituted phenoxypyrimidine and 3 mol equiv of the diazo ester. The ortho-alkylated derivatives of phenoxy products possessing the ester functionality undergo decarboxylative pyrimidine/pyridine migratory cyclization (rather than deprotection of pyrimidine/pyridine group) using 20% NaOEt in EtOH affording a novel class of 3-(pyrimidin-2(1H)-ylidene)benzofuran-2(3H)-ones and 6-methyl-3-(pyridin-2(1H)-ylidene)benzofuran-2(3H)-one. The ortho-alkylated phenoxypyridine possessing ester functionality also undergoes decarboxylative pyridine migratory cyclization using MeOTf/NaOMe in toluene providing 6 methyl-3-(1-methylpyridin-2(IH)-ylidene)benzofuran-2 (3H)-one.
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