Synthesis of azaindoles
An efficient protecting-group-free two-step route to a broad range of aza- and diazaindoles was established, starting from chloroamino-N-heterocycles. The method involves an optimized Suzuki-Miyaura coupling with (2-ethoxyvinyl)borolane followed by acetic acid-catalyzed cyclization.
D. K. Whelligan, D. W. Thomson, D. Taylor, S. Hoelder, J. Org. Chem., 2010, 75, 11-15.
An effective reductive alkylation of electron-deficient o-chloroarylamines was developed. The derived N-alkylated o-chloroarylamines were elaborated to N-alkylazaindoles and N-alkylindoles via a novel one-pot process comprising copper-free Sonogashira alkynylation and a base-mediated indolization reaction.
M. McLaughlin, M. Palucki, I. W. Davies, Org. Lett., 2006, 8, 3307-3310.
A practical and straightforward preparation of various novel 2-substituted 7-azaindole derivatives from 2-amino-3-iodopyridine by a two-step procedure is described that gives the desired compounds in good overall yields.
M. C. de Mattos, S. Alatorre-Santamaría, V. Gotor-Fernández, V. Gotor, Synthesis, 2007, 2149-2152.
A new, mild, and efficient method for the synthesis of polyfunctionalized indoles by direct reaction of substituted 2-chloroanilines with cyclic or acyclic ketones was developed. This procedure is simple to carry out and broadly applicable.
M. Nazare, C. Schneider, A. Lindenschmidt, D. W. Will, Angew. Chem. Int. Ed., 2004, 43, 4526-4528.
A robust and flexible synthesis of 1,3- and 1,3,6-substituted 7-azaindoles is presented starting from nicotinic acid derivatives or 2,6-dichloropyridine, respectively. Microwave heating dramatically accelerates the penultimate reaction step, an epoxide-opening-cyclization-dehydration sequence.
H. Schirok, J. Org. Chem., 2006, 71, 5538-5545.