期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 351, 期 1-2, 页码 85-88出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200800568
关键词
alkynes; cyclization; regioselectivity; silver
资金
- National Natural Science Foundation of China [20702015]
- Shanghai Municipal Committee of Sciences and Technology [07pj14039]
- Shanghai Shuguang Program [07SG27]
- Shanghai Leading Academic Discipline Project [B409]
A dramatic substituent effect was found in the silver(I)-catalyzed cyclization reaction of ortho-alkynylaryl aldehyde oxime derivatives. When R is an alkyl group, the Ag(I)-catalyzed reaction in dimethylacetamide at 110 degrees C (conditions A) affords isoquinolines in good to excellent yields, in contrast, isoquinolin-1(2H)-ones were produced in moderate to high yields under conditions B (dimethylformamide, room temperature) when R is an acetyl group. A plausible mechanism was proposed for this product selectivity control reaction (PSCR) by subtle structure modification.
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