Preparation of 2-substituted pyrroles and indoles by regioselective alkylation and deprotection of 1-(2-trimethylsilyllethoxymethyl)pyrrole and 1-(2-trimethylsulylethoxymethyl) indole
After N-alkylation of pyrrole and indole with 2-trimethylsilylethoxymethyl chloride the products of the reaction could be regioselectively deprotonated with n-butyllithium at the 2-position.Reaction of the resulting anions with acid chlorides, lactones, silyl chlorides or aldehydes gave addition products, some of which were deprotected to the parent pyrrole or indole using anhydrous tetra-n-butylammonium fluoride.
Edwards, Martin P.,Doherty, Annette M.,Ley, Steven V.,Organ, Helen M.
p. 3723 - 3730
(2007/10/02)
Protecting Groups for the Pyrrole and Indole Nitrogen Atom. The methyl Moiety. Lithiation of 1-methyl>pyrrole
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Muchowski, Joseph M.,Solas, Dennis R.
p. 203 - 205
(2007/10/02)
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