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|Title:||Silica gel-mediated hydroamination/semipinacol rearrangement of 2-alkylaminophenylprop-1-yn-3-ols : synthesis of 2-oxindoles from alkynes and 1-(2-aminophenyl) ketones||Authors:||Susanti, Dewi
Ng, Linda Li Ru
Chan, Philip Wai Hong
|Keywords:||DRNTU::Science::Chemistry::Organic chemistry||Issue Date:||2014||Source:||Susanti, D., Ng, L. L. R., & Chan, P. W. H. (2014). Silica gel-mediated hydroamination/semipinacol rearrangement of 2-alkylaminophenylprop-1-yn-3-ols : synthesis of 2-oxindoles from alkynes and 1-(2-aminophenyl) ketones. Advanced Synthesis & Catalysis, 356(2-3), 353-358.||Series/Report no.:||Advanced synthesis & catalysis||Abstract:||2-Alkylaminophenylprop-1-yn-3-ols, prepared from the lithium diisopropylamide (LDA)-mediated 1,2-addition of alkynes to 1-(2-aminophenyl) ketones, can be converted to 3,3-disubstituted 2-oxindoles by using silica gel in n-hexane/ethyl acetate (20:1 v/v) as the reaction medium. The utility of the approach as a potential scale-up strategy for the synthesis of 2-oxindoles was exemplified by the large-scale synthesis of one adduct in excellent yield. The synthetic applicability of this chemistry was also demonstrated by the recycling of the silica gel up to 8 times with no apparent loss of activity being observed for the same example.||URI:||https://hdl.handle.net/10356/102861
|ISSN:||1615-4150||DOI:||10.1002/adsc.201300911||Rights:||© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.||Fulltext Permission:||none||Fulltext Availability:||No Fulltext|
|Appears in Collections:||SPMS Journal Articles|
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