Antimicrobial activity tests of dihydroazeto[2′,3′:4,5]seleno[2,3-
Literature survey reveals that sulfur- and selenium-containing molecules have attracted great importance in synthetic organic chemistry; particularly, aromatic five- and six-membered heterocycles fused or bridged to quinoline ring in linear fashion are found in many natural products due to their great pharmacological importance [1, 2, 3, 4, 5, 6, 7].
Substituted 2-azetidinone is an important class of compound for its importance in β-lactam antibiotic synthesis [8, 9, 10]. β-Lactam drugs in heterocycles are still the most widely prescribed antibiotics used in medicine . The discovery of penicillin 2-azetidinone-based heterocycles have been one of the main classes of drugs with wide therapeutic activities, viz. anticonvulsant , anti-inflammatory , antibacterial , herbicidal , and also functioning as enzyme inhibitor  and are effective on central nervous system.
The conversion of aryl quinolines into dihydroazeto[2′,3′:4,5]seleno[2,3-
In continuation of our research program directed toward the studies on Sulfur Chemistry [17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30] and synthesis of new potentially bioactive molecules, we were in need of a medicinal, bioorganic, industrial, cost-effective and commercial method for the synthesis of quinoline-based sulfur and selenium compounds. Also, the extensive biological properties and pharmaceutical applications have attracted interests in development of such sulfur and selenium-containing analogs.
2. Results and discussions
In this contribution, we focused our attention on the fast and efficient synthesis of dihydroazeto[2′,3′:4,5]seleno[2,3-
In the current investigation very interesting result was observed in the reaction of
IR spectra were taken on a Perkin Elmer 157 Infrared spectrophotometer. 1H NMR spectra (300 MHz) were recorded on a Bruker supercon FT-NMR instrument using TMS as internal standard and mass spectra on a Jeol JMS-D 300 mass spectrometer operating at 70 eV. Melting points were determined in open capillary and are uncorrected. Purity of the compounds was checked by TLC on silica gel and the compounds were purified by column chromatography.
3.1 Preparation of sodium hydrogen selenide
A mixture of 1 g of selenium powder and 25 ml of water was taken in a 500 ml beaker. The heat obtained was controlled by keeping this mixture at ice cold condition. A calculated amount of sodium borohydride of 0.026 moles was added in stepwise with constant stirring. During this, immediate liberation of foaming takes place because of the formation of hydrogen gas. Once the addition of sodium borohydride is over, approximately 25 ml of water was added along the side of the beaker and stirring was continued over 15 min. During this, a colorless, deep, reddish NaHSe formed and thus the obtained result was used without further any purification.
3.2 Preparation of dihydroazeto[2′,3′:4,5]seleno[2,3-
b]quinolines ( 2a: E)
About 0.01 mole of azitidone
Solid, mp. 280°C; 1H NMR (300 MHz, DMSO-
Solid, mp. 272°C; 1H NMR (300 MHz, DMSO-
Solid, mp. 287°C; 1H NMR (300 MHz, DMSO-
Solid, mp. 292°C; 1H NMR (300 MHz, DMSO-
Solid, mp. 288°C; 1H NMR (300 MHz, DMSO-
4. Antimicrobial activity
The in vitro antimicrobial activity was carried out against 24 h old cultures of three bacteria by disk diffusion method  using ampicillin as the reference. Compounds