Acetals of lactams and amides of acids. Communication 80. Investigation of alkylation of 2,4-diaminopyridine derivatives. Unconventional synthesis of substituted imidazo[1,2-a]pyridine

Synthesis of pyrido[3′,2′:4,5]pyrrolo-and pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine derivatives using the thorpe-ziegler cyclization reaction

“…Similar syntheses of pyrrolo-and thieno [2,3-b]pyridines in other systems were also described [3,5]. …”

Design and Synthesis of New Templates Derived from Pyrrolopyrimidine as Selective Multidrug-Resistance-Associated Protein Inhibitors in Multidrug Resistance

“…21 was synthesized from 2-chloro-4-methylaminopyridine-3-nitrile (20) according to a reported method. 6 3-Amino-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic Acid Ethyl Ester (22). To a solution of 3-amino-4-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (9.95 g, 39.2 mmol) in ethanol (400 mL) was added 10% palladium on carbon (800 mg) as a slurry in ethanol under argon.…”

“…Mp 238-239 °C; 1 H NMR (CDCl3) δ 1.68-1.75 (m, 4H, 2 × CH2), 2.58-2.76 (m, 8H, 4 × CH2), 3.00-3.06 (m, 4H, 2 × CH2), 3.69-3.73 ((m, 4H, 2 × CH2), 6.82 (m, 1H, ArH), 6.90-7.00 (m, 2H, 2 × ArH), 7.44 (d, 1H, J ) 8. 6 ture of compound 51 (0.5 g, 1.19 mmol), sodium hydroxide solution (1 M, 1.2 mL), and 30% hydrogen peroxide solution (0.7 mL) was stirred in methanol (30 mL) for 3 days. Saturated sodium carbonate solution was added, resulting in a precipitate, which was collected by filtration to yield a crude product that was purified using flash chromatography to yield the title compound (0.475 g, 90% (3,ethyl]piperazin-1-yl}-9H-2,4,9-triazafluorene-5-carboxylic acid amide 52 (100 mg, 0.28 mmol) and 4-bromopyridine hydrochloride (1.1 equiv, 49 mg) were suspended in 1,4-dioxane (1.5 mL).…”

“…5 Compound 68 was prepared by treatment of the 6-nitro derivative of compound 6 (R ) 6-NO 2, R′ ) H) with ethyl bromoacetate following the general alkylation procedure and subsequent coupling with 13 using the general protocol. 2 1 H NMR (CDCl3) δ 1.25 (t, 3H, J ) 6.9 Hz, CH3), 2.70-2.85 (m, 8H, 4 × CH2), 3.50 (m, 4H, 2 × CH2), 4.25 (q, 2H, J ) 6.9 Hz, CH2), 5.25 (s, 2H, CH2), 6 72). Sodium (0.021 g, 0.91 mmol) was dissolved in MeOH (5 mL), to which was added compound 29 (0.06 g, 0.135 mmol).…”

“…Thus, methylaminochloropyridine nitrile 20 was alkylated with bromoethyl acetate 18 and simultaneous cyclization gave the amino ester 21 , which was dechlorinated by hydrogenolysis to give 22 . Methoxypyridine analogue 25 was also obtained by the displacement of the chloro group of 21 with sodium methoxide.…”