Journal
TETRAHEDRON
Volume 57, Issue 1, Pages 109-118Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(00)00993-5
Keywords
allylsilanes; quinolines; chloroformate
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Addition reactions of allylsilanes to quinolines acylated by chloroformate esters are promoted by a catalytic amount of triflate ion to give 2-allyl-1,2-dihydroquinoline derivatives in good yields. A variety of functional groups on quinoline ring are tolerated in the reaction. The similar reactions of allylsilanes with isoquinolines afford cyclized benzoisoquinuclidine derivatives in good yields, along with 1-allyl-1,2-dihydroisoquinoline derivatives, depending on the reaction conditions. In addition, 2-substituted allylic silanes can be utilized in the present addition reactions to afford the 2-substituted and 1-substituted 1,2-dihydro-quinolines and -isoquinolines, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.
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