Yakhontov, L. N.; Azimov, V. A.; Lapan, E. I. published the artcile< Reactivity of isomeric azaindoles>, HPLC of Formula: 23612-36-4, the main research area is indoles aza; pyridines; azaindoles; furopyridines; pyrrolopyridines; pyridines pyrrolo.
Treatment of the pyridine I (R = 6-Cl) with NH3 in EtOH 4 hrs. at 200° yielded 71.5% 5-azaindoline (II) (R = 6-Cl, R1 = H), m. 106-7° (EtOAc), b1·5 152-4°. The azabenzofuran III (R = 6-OH) heated 8 hrs. at 190° with 3 molar equivalents PhCH2NH2 yielded 72% II (R = 6-OH, R1 = CH2Ph), m. 187-8° (dioxane), transformed by heating 5 hrs. at 150° with POCl3 into II (R = 6-Cl, R1 = CH2Ph), m. 75-6° (EtOAc). This reduced over Pd-C gave II (R = R1 = H) (IV), m. 102-3° (C6H12), dehydrogenated by heating 15 min. (N atm.) with 9% Pd-C at 2 5-25° to yield 70.5% 5-azaindole (V), m. 109.5-10.0° (H2O). III (R = OH) heated 8 hrs. at 250° with PhNH2 gave 78.8% II (R = 6-OH, R1 = Ph), m. 215-16° (EtOH), converted via II (R = 6-Cl, R1 = Ph), m. 99-100° (EtOH) into II (R = H, R1 = Ph), m. 59-60° (petroleum ether) and dehydrogenated at 255-65° to yield 80.7% 1-phenyl-5-azaindole (VI), m. 58-9° (petroleum ether). Condensation of 2-methyl-3-nitropyridine with (CO2Et)2 in the presence of EtOK in C6H6 at 25° 24 hrs. and the product, 70% Et3-nitro-2-pyridylpyruvate, m. 126-7°, reduced in EtOH over 9% Pd-C gave quant. Et 4-azaindole-2-carboxylate, m. 173-3.5°, saponified to 4-azaindole-2-carboxylic acid (VII), m. 302-3° (decomposition). Similarly, 2-methyl-3-nitro-6-ethoxypyridine, m. 39-40°, gave 58.8% Et 3-nitro-6-ethoxy-2-pyridylpyruvate, m. 131-2° (alc.), which gave 93% Et 5-ethoxy-4-azaindole-2-carboxylate, m. 148-9.5° (alc.) and then, via the corresponding acid, m. 300° (decomposition), 5-ethoxy-4-azaindole (VIII), m. 148-50°. Nitration, bromination, cyanomethylation and the Mannich reaction were used as electrolytic substitution reactions and carried out under conditions which had given the best yields for the corresponding 7-azaindole derivatives The cyanomethylated products were converted into azoindolyl-3-acetic acids. The Mannich reactions were carried out with 20% paraformaldehyde and 3 molar equivalents Me2NH.-HCl in refluxing BuOH; % yields and m.p. for the 3-substituted products were tabulated. π-Electron d. effects were discussed.
Tetrahedron Letters published new progress about Reactivity (chemical). 23612-36-4 belongs to class pyridine-derivatives, and the molecular formula is C7H5BrN2, HPLC of Formula: 23612-36-4.