Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/102861
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
http://hdl.handle.net/10220/19218
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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