Convenient and Scalable Synthesis of 2,3-Dihydroquinazolin-4(1H)-one Derivatives and Their Anticancer Activities

An efficient and mild InBr₃-catalyzed approach to synthesize 2,3-dihydroquinazolin-4(1H)-one derivatives (3a–3aa) has been developed. Notably, all the products were isolated by recrystallization and the reaction is accessible on a gram scale. Moreover, the reactions only require 10–60 min. All the synthesized compounds were evaluated for their in vitro anticancer activity against four human cancer cell lines.     

Water-Mediated Synthesis of Benzazole and Thiourea Motifs by Reacting Naturally Occurring Isothiocyanate with Amines

An efficient, green, and facile method has been developed for the synthesis of benzazole and thiourea analogues from naturally occurring erucin in moderate to good yields. The reaction was carried out in water without using any metal catalyst or base. The present method tolerated the various functional groups on aromatic rings and also applicable for other isothiocyanates.     

A Mild and Efficient Route to 3-Vinylchromones in Aqueous Micellar Media

A simple, mild, and ecofriendly method has been developed for the synthesis of 3-vinylchromones from 4-oxo-4H-1-benzopyran-3-carboxaldehyde (3-formylchromone) by simple Knoevenagel condensation with various active methylene compounds (AMC) in aqueous micellar media in the presence of catalytic amounts of cetyl trimethylammonium bromide (CTAB) and 1,4-diazabicyclo[2.2.2]octane (DABCO). In the case of malonic acid as AMC, the reaction resulted in formation of only Doebner decarboxylated products under the standard reaction condition. It has been also observed that 3-formylchromone derivatives primarily undergo tandem Knoevenagel and Michael reactions in the presence of > 2 equiv. of ethyl acetoacetate to produce benzophenone derivatives, by opening of pyran ring, as the sole product in good yields.     

Synthesis of Some 2-(3-Alkyl/aryl-5-trifluoromethylpyrazol-1-yl)-4-(coumarin-3-yl)thiazoles as Novel Antibacterial Agents

Abstract

Herein, we describe a one-pot synthesis of some novel 2-(3-alkyl/aryl-5-trifluoromethylpyrazol-1-yl)-4-(coumarin-3-yl)thiazoles (6) involving the reaction of 3-alkyl/aryl-5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazole-1-thiocarboxamides (3) with 3-bromoacetylcoumarins (5) in the presence of sodium carbonate in ethanol. Reaction of 3 with 5 in the absence of sodium carbonate, however, resulted in the formation of 2-(3-alkyl/aryl-5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(coumarin-3-yl)thiazoles, which were subsequently dehydrated to 6 by refluxing in ethanol in the presence of sodium carbonate. The structure of the synthesized compounds (6) was confirmed by infrared (IR), mass, ¹H NMR, and ¹³C NMR spectra and elemental analysis data. Newly synthesized compounds (6) showed moderate to good activity against Gram-positive bacteria.     

A new form of discotic metallomesogens: the synthesis of metal-bridged triphenylene discotic dimers

Discotic metallomesogens are becoming increasingly important due to their electronic and optoelectronic properties. Preliminary results on the synthesis and characterization of a new form of discotic metallomesogens in which a Hg atom is covalently linked with two substituted triphenylene moieties are presented.     

Liquid crystalline banana‐shaped monomers derived from 2,7‐naphthalene: synthesis and properties

Three banana‐shaped monomers, i.e. 2,7‐naphthalene bis[4‐(4‐allyloxyphenylazo)‐benzoate], 2,7‐naphthalene bis[4‐(4‐allyloxy‐3‐fluorophenylazo)benzoate] and 2,7‐naphthalene bis{4‐[4‐(10‐undecenyloxy)phenylazo]benzoate}, containing azobenzene as side arms, 2,7‐dihydroxynaphthalene as central units and terminal double bonds as polymerisable functional groups, were synthesised and their mesophase behaviour investigated. Polarizing optical microscopy and DSC measurements reveal that all compounds exhibit nematic mesophases. The absorption spectrum of the trans‐azobenzene groups displays a high‐intensity π–π* transition at about 365 nm and a low‐intensity n–π* transition at around 450 nm for all compounds. Hence, photochromism can be achieved by the introduction of the azo linkage to banana‐shaped liquid crystals molecules.     

Effect of an electric field on defects in a nematic liquid crystal with variable surface anchoring

We report experimental studies on defects in a nematic liquid crystal with negative dielectric anisotropy mounted in a cell with perfluoropolymer-coated surfaces. The sample exhibits a discontinuous anchoring transition from planar to homeotropic on cooling at zero or a small electric field, and above a cross-over voltage a continuous ‘inverse Freedericksz transition’, at which the director starts tilting in opposite directions at the two surfaces. Defects of strength ±1/2 are either annihilated or expelled when the director tilts. On the other hand, disclination lines of ±1 which end in partial point defects (boojums) at the surfaces in the planar alignment regime acquire point defects of strength ±1 at the midplane of the cell when the director tilts. At a low enough temperature, the homeotropic anchoring becomes strong, and an electric field above the Freedericksz threshold generates the usual umbilic defects, which follow the dynamic scaling laws found in earlier studies.     

Synthesis,characterisation and mesomorphic properties of ester containing aroylhydrazones and their nickel(II) complexes

A new series of mesogenic aroylhydrazone-based ligands, N-[4-(4′-alkoxy)benzoyloxybenzylidene]-N′-[4″-alkoxybenzoyl]hydrazine with either the same or different peripheral alkyl chains, and nickel(II) complexes of some of them have been synthesised. They were characterised by elemental analyses, Fourier transform infrared, proton and carbon nuclear magnetic resonance and ultraviolet-visible spectroscopy. The mesomorphic properties of these compounds were investigated by differential scanning calorimetry and polarising optical microscopy. All the aroylhydrazones, except those with no lateral chains on either end of the molecule and where m?=?n?=?14, 16, exhibit a monotropic or enantiotropic smectic C mesophase, which are almost insensitive to the peripheral alkoxy chain length. The square planar nickel(II) complexes of the ligands show only an isotropic phase at higher temperature (>175°C) and no mesogenic nature is observed. Density functional theory calculations have been performed using the GAUSSIAN-03 program at the Becke, three-parameter, Lee–Yang–Parr level to obtain the stable electronic structure of the ligand.     

T-shaped non-symmetrical twin liquid crystalline compounds

New unconventional T-shaped non-symmetrical dimeric liquid crystalline compounds have been synthesised and their thermotropic properties studied on the hot-stage of a polarising microscope. These compounds consist of an azo-ester mesogenic unit with a range of terminal substituents (–CH₃, –OCH₃, –NO₂ or –Cl) at one end, interconnected by a flexible spacer (n?=?4, 5 or 10) via ether and ester linking units to a biphenyl moiety at the lateral hydroxyl position of the azo-ester. All the compounds were characterised using a combination of elemental analysis and standard spectroscopic methods. The compounds were found to exhibit enantiotropic nematic and smectic mesophases. The effect of different terminal substituents on mesomorphism is discussed.