Synthesis and antimicrobial activity of some new pyrimidinone and oxazinone derivatives fused with thiophene rings using 2-chloro-6-ethoxy-4-acetylpyridine as starting material.

A series of pyridines, pyrimidinones, oxazinones and their derivatives were synthesized as antimicrobial agents using citrazinic acid (2,6-dihydroxyisonicotinic acid) as a starting material. α,ß-Unsaturated ketones 3a-c were condensed with cyanothio-acetamide in the presence of ammonium acetate to give 2-cyanopyridinethiones 4a-c, which were reacted with ethyl chloroacetate to yield the corresponding cyano esters 5a-c. The esters 5a-c were cyclized by action of sodium methoxide to aminoesters 6a-c, which were aminolyzed with ammonia to corresponding aminoamide derivatives 7a-c. Also, the esters 6a-c were hydrolyzed with NaOH to the corresponding sodium salt 8a-c, which were treated with acetic anhydride to afford 2-methyloxazinones 9a-c. The latter compounds were treated with ammonium acetate to afford 2-methylpyrimidinones 10a-c, followed by methylation with methyl iodide to yield 2,3-dimethyl-pyrimidinones 11a-c. The antimicrobial screening showed that many of these compounds have good antibacterial and antifungal activities comparable to streptomycin and fusidic acid used as reference drugs.

In situ synthesis, photometric and spectroscopic studies of chelating system during the 1,4,7,10,13,16-hexaoxacyclooctadecane charge transfer reaction with different acceptors.

Electron donor acceptor complexes (EDA) of the 1,4,7,10,13,16-hexaoxacyclooctadecane (18-crown-6) as a rich donor were spectrophotometrically discussed and synthesized in solid form according the interactions with different nine of usual π-acceptors like 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione (p-chloranil; p-CHL), tetrachloro-1,2-benzoquinone (o-chloranil; o-CHL), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), tetracyanoquinodimethane (TCNQ), 2,6-dichloroquinone-4-chloroimide (DCQ), 2,6-dibromoquinone-4-chloroimide (DBQ), 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone (chloranilic acid; CLA), N-bromosuccinimide (NBS), 2,4,6-trinitrophenol (picric acid; PA). Spectroscopic and physical data such as formation constant (K(CT)), molar extinction coefficient (ɛ(CT)), standard free energy (ΔG°), oscillator strength (f), transition dipole moment (µ), resonance energy (R(N)) and ionization potential (I(p)) were estimated in chloroform or methanol at 25°C. Based on the elemental analysis and photometric titrations the CT-complexes were formed indicated the formation of 1:1 charge-transfer complexes for the o-CHL, TCNQ, DCQ, DBQ and NBS acceptors but 1:3 ratio for p-CHL, DDQ, CLA and PA, respectively. The charge-transfer interactions were interpretative according to the formation of dative ion pairs [18C6(•+), A(•-)], where A is acceptor. All of the resulting charge transfer complexes were isolated in amorphous form and the complexes formations on IR and (1)H NMR spectra were discussed.