The synthesis of a series of substituted 9H-carbazoles by the photostimulated S(RN)1 substitution reaction with diarylamines as starting substrate was performed. The diarylamines were obtained by two approaches, the Pd-catalyzed reactions (Buchwald-Hartwig) or Cu-catalyzed reactions of 2-haloanilines with aryl halides, or 2-bromoiodobenzene with anilines, with moderate to very good isolated yields (45-89%). Through an intramolecular C-C bond formation of diarylamines by the S(RN)1 mechanism, carbazoles were achieved. These reactions proceeded synthetically in very good to excellent yields (81-99%) in liquid ammonia and DMSO. The reaction of N-(2-bromophenyl)-2-phenylbenzenamine gave 1-phenyl-9H-carbazole (38%) and the isomer 9H-tribenz[b,d,f]azepine (58%). By using this methodology, 9H-carbazoles, substituted 9H-carbazoles, benzocarbazoles, and even 3,3'-bi(9H-carbazole) were obtained by a double S(RN)1 reaction with benzidine.

A novel series of neutral and cationic dimeric surfactants were prepared involving ketalization reaction, Williamson etherification, and regioselective oxirane ring opening with primary and tertiary alkyl amines. The critical micelle concentration (CMC), effectiveness of surface tension reduction (g CMC ), surface excess concentration (G), and area per molecule at the interface (A) were determined and values indicate that the cationic series is characterized by good surface-active and self-aggregation properties. For the first time, we reported the antimicrobial activities against representative bacteria and fungi for dimeric compounds. The antimicrobial activity was found to be dependent on the target microorganism (Grampositive bacteria > fungi > Gram-negative bacteria), as well as both the neutral or ionic nature (cationic > neutral) and alkyl chain length (di-C 12 > di-C 18 > di-C 8 ) of the compounds. The cationic di-C 12 derivative was found to have equipotent activity to that of benzalkonium chloride (BAC) used as standard. Murguía, V.A. Vaillard, V.G. Sánchez et al. method, surface-active properties, and the antimicrobial activity of neutral and cationic series of new gemini compounds having a flexible, hydrophilic spacer and two alkyl chains of varying length. The molecular design and synthetic strategy were outlined to link the two hydrophilic head groups through a spacer having multiple oxygen atoms (1,3-dioxane ring, ether, and hydroxyl groups) conferring wettable properties. The structures of the synthesized compounds are illustrated in . EXPERIMENTAL PROCEDURES 1All the chemicals used in synthetic procedures were of reagent grade quality and used as received. 21 5 5 5 3 3 2 The reaction was carried out in a 100 mL three-neck round-bottomed flask equipped with a magnetic stirring bar and a Dean-Stark trap topped with a condenser 24,25) . A catalytic amount of p-toluenesulfonic acid monohydrate (5% w/w relative to the cyclohexanone) was added to a pentaerythritol (2.995 g, 22 mmol) and benzene-dimethylformamide (40 : 60) mixture (50 mL) at room temperature. The well-stirred dispersion was warmed to 80 until complete dissolution, and cyclohexanone (1.571 g, 15 mmol) was then added dropwise while the reaction mixture was heated to 115 for 48 hours. The water formed during the reaction was removed by distillation and collected in the Dean-Stark trap. The reaction was stopped when there was no further increase in the collected water. After cooling, the reaction mixture was poured into water (30 mL), neutralized with potassium carbonate and three-fold extracted with dichloromethane (30 mL). The organic layer was dried with MgSO 4 and evaporated in vacuo. After Kugelrohr distillation and column chromatography on silica gel by eluting with ether-light petroleum (80 : 20) mixture, the compound was obtained as a white solid in good yield (90 %) and good selectivity (92 %). (13), 173 (96), 160 (4), 125 (5), 101 (6), 99 (14), 83 (34), 71 (40), 55 (100), 41 (72) 26,27) . A 1 : 10 : 6 : 0.1 molar ...

The synthesis of a series of 6-substituted 2-pyrrolyl and 2-indolyl benzoxazoles by photostimulated C-O cyclization of anions from 2-pyrrole carboxamides, 2-indole carboxamides, or 3-indole carboxamides has been found to proceed in good to excellent yields (41-100%) in DMSO and liquid ammonia. The pyrrole and indole carboxamides are obtained in good to very good isolated yields by an amidation reaction of different 2-haloanilines with 2-carboxylic acid of pyrrole and 2- or 3-carboxylic acid of indole. To explain the regiochemical outcome of these reactions (C-O arylation vs C-N or C-C arylation), a theoretical analysis was performed using DFT methods and the B3LYP functional.