The Synthesis and Antibacterial Activity of Novel 4-Pyrrolidin-3-cyanopyridine Derivatives

Abstract

in Wiley Online Library (wileyonlinelibrary.com).2-Bromo-4-(pyrrolidin-1-yl)pyridine-3-carbonitrile obtained from 2-(1,3-bis(pyrrolidin-1-yl)allylidene) malononitrile has been used as a substrate for the synthesis of new cyanopyridine derivatives: 2-methoxy, 2-phenoxy, 2-aminoethylthio, and 2-thioxo. 4-(Pyrrolidin-1-yl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile 7 in reaction with suitable alkyl and aminoalkyl halides gave respective sulfides. All synthesized compounds were evaluated for their antimicrobial activity against 26 aerobic and anaerobic bacteria. Determined minimal inhibitory concentration values ranged from 6.2 to 100 mg/mL. Derivatives 1, 3, 4, 6, and 12 were the most active compounds.J. Heterocyclic Chem., 50, 544 (2013). RESULTS AND DISCUSSIONMittelbach [13] reported the cyclization of 1,1-dicyano-4-(N,N-dimethylamino)-2-methoxy-1,3-butadiene with ammonia to give 2-amino-3-cyano-4-methoxypyridine (Scheme 1). We attempted the analogous cyclization of 1,1-dicyano-4-(N, N-dimethylamino)-2-methoxy-1,3-butadiene with pyrrolidine.The pyrrolidine ring should end up in 2-position of the pyridine ring, keeping the methoxy group in 4-position. Surprisingly, instead of the expected product, we obtained butadiene 1, the structure of which was confirmed by 1 H NMR spectroscopy and X-ray crystallography.The skeleton of 1 consists of conjugated system of single and multiple bonds including two pyrrolidine N atoms, which participate in the conjugation through their

Synthesis of alkynyl/alkenyl-substituted pyridine derivatives via heterocyclization and Pd-mediated Sonogashira/Heck coupling process in one-pot: a new MCR strategy

“…The study reveal that lower yields of nal products (7a-d) are obtained due to steric hindrance in the course of the C-C coupling process. It is found that lower yields of products (7a-d) are offered in all cases (entries 1-4, Table 3) irrespective of the nature of substituents present on terminal alkyne substrates (5a, 5b, 5f and 5i) when 2-bromobenzandehyde (1a) is used instead of 3-bromobenzandehyde (1).…”

Synthesis and Antibacterial Activity of 2-(Substituted phenyl)-5-(pyridin-4-yl)-1,3,4-oxadiazoles

“…Heterocyclic system containing pyridine ring, constitute an important class of potentially bioactive compounds. The earlier workers reported that, pyridine derivatives are associated with a wide spectrum of biological activities viz antimicrobial 1-2 , anti-inflammatory 3 , antibacterial 4 , anti-parkinsonian 5 , anticonvulsant 6 , analgesic 7 etc. Similarly oxadiazole have shown a wide range of applications in drug development against convulsant 8 , inflammatory 9 , bacterial [10][11] and microbial [12][13] etc.…”