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DOI: 10.1055/s-2003-40884
Synthesis of 2-Aryl-1-hydroxyazaindoles and 2-Arylazaindoles via Oxidation of o-Hydroxyaminostyrylpyridines
Publikationsverlauf
Publikationsdatum:
25. Juli 2003 (online)
Abstract
2-Aryl-1-hydroxyazaindoles (pyrrolopyridin-1-ols) are prepared via an oxidation/cyclization of o-hydroxyaminostyrylpyridines with DDQ. Reduction of the N-OH bond affords the corresponding 2-arylazaindoles (1H-pyrrolopyridines). The scope of the cyclization is explored via (i) the condensation of 4-methyl-3-nitropyridine with various aryl aldehydes to afford 2-aryl substituted 6-azaindoles and, (ii) the synthesis of 2-phenyl-4-, 5- and 7-azaindoles.
Key words
azaindoles - 1N-hydroxy azaindoles - cyclization - oxidation - 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) - pyrrolopyridines
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