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Synlett 2000; 2000(12): 1788-1792
DOI: 10.1055/s-2000-8671
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Directed Metallation Studies on Heteroaromatic Systems. Synthesis of 2,3-Disubstituted Furan, Thiophene, N-Methylpyrrole and N-Methylindole

T. Grimaldi* , M. Romero, M. D. Pujol
  • *Laboratori de Química Farmacèutica, Facultat de Farmàcia, Universitat de Barcelona, Av. Diagonal 643, 08028 Barcelona, Spain; Fax +(93)4 03 59 41; E-mail: mdpujol@farmacia.far.ub.es
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Publication Date:
31 December 2000 (online)

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A general method for the preparation of 2,3-disubstituted furan, thiophene, N-methylpyrrole and N-methylindole has been developed, from the corresponding carboxamides and carboxylic acids, by reaction with organolithium reagents. Efficient and selective procedure has been reported using tert-butyllithium and secondary amides.

heterocyclic compounds - directed metallation - tert-butyllithium - secondary and tertiary amides - furan - thiophene - pyrrole - indole