94145-22-9Relevant academic research and scientific papers
AZAINDOLE DERIVATIVES. 66. 1,6-DISUBSTITUTED 4-METHYL-5-CYANO-7-AZAINDOLINES
Sycheva, T. V.,Yakhontov, L. N.
, p. 68 - 72 (2007/10/02)
A general method was developed for the synthesis of 1,6-disubstituted 4-methyl-5-cyano-7-azaindolines from the readily available ammonium salt of 2,6-dihydroxy-3-(β-hydroxyethyl)-4-methyl-5-cyanopyridine through the corresponding N-substituted ammonium salts and N-substituted 2-amino-3-(β-hydroxyethyl)-4-methyl-5-cyano-6-hydroxypyridines with treatment of the latter by POCl3.This method gives a 40percent yield of 4-methyl-5-cyano-7-azaindoline compounds containing various aralkyl or alkyl substituents at N-1 and a hydroxy group or halogen atom at C-6 in three steps.
DERIVATIVES OF AZYINDOLES. 65. SYNTHESIS OF 1-BENZYL-4-METHYL-5-CYANO-6-HYDROXY-7-AZAINDOLINE
Sycheva, T.V.,Kuleshova, E.F.,Yakhontov, L.N.
, p. 901 - 905 (2007/10/02)
Treatment of the ammonium (I) or benzylammonium salt of 2,6-dihydroxy-3-(β-hydroxyethyl)-4-methyl-5-cyanopyridine (II) with a mixture of benzylamine and phosphorus pentoxide yielded 2-benzylamino-3-(β-hydroxyethyl)-4-methyl-5-cyano -6-hydroxypyridine (III), which, when heated with phosphorus oxychloride, is converted to 1-benzyl-4-methyl-5-cyano-6-hydroxy-7-azaindoline (IV).The products of thermal fragmentation of II with benzylamine were studied by the method of chromato-mass spectrometry.In addition to compound III, N,N'-dibenzylurea (V) and the dibenzylamide of malonic acid (VI) were preparatively isolated from the reaction products .The cyclization of I and II to 4-methyl-6-hydroxy-2,3-dihydro-7-azabenzofuran (VII) and 4-methyl-5-cyano-6-hydroxy-2,3-dihydro-7-azabenzofuran (VIII) was carried out.Heating VIII with benzylamine at 200-210 grad C led to compound III.
