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Preparation of 2-(4-fluorobexzyl)-6-(4-nitrophenyl)imidazo[2,1-b][1,3,4]thiadiazole is described and its crystal structure is discussed. The compound crystallizes in the monoclinic space group C2/c with a = 39.941(6) Å, b = 5.698(2) Å, c = 13.272(5) Å β = 90.880°, V = 3020(2) Å3, z = 8. The crystal structure is stabilized by weak intermolecular C-H...N,C-H...O,C-H...S, and C-H...F interactions. [ABSTRACT FROM AUTHOR]

The crystal and molecular structure of 2-(4-fluoro-benzyl)-6-phenyl-imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde is described. The compound crystallizes in the monoclinic space group P21/n with a = 7.419(3)Å, b = 8.287(3)Å, c = 25.734(10)Å, β = 91.686(8)°, V = 1,581.6(10)Å3, z = 4. The crystal structure is stabilized by intermolecular C-H...N, C-H...O, and C-H...F interactions. [ABSTRACT FROM AUTHOR]

Novel classes of 3-(6-Aryl-5-phenylsulfanylimidazo[2,1-b][1,3,4]thiadiazol-2-yl-methyl)-benzo[d]isoxazoles(2a–f)and 3-(5-Benzenesulfonyl-6-arylimidazo[2,1-b][1,3,4] thiadiazol-2-yl-methyl)-benzo[d]isoxazoles(3a–f)have been synthesized. The sulfide derivatives (2a–f) were obtained by the nucleophilic substitution of bromo derivatives (1a–f) with thiophenols, and sulfone derivatives (3a–f) were obtained by the oxidation of2a–f.All the newly synthesized compounds were characterized by elemental analysis, infrared, nuclear magnetic resonance, and mass spectroscopic data. Furthermore, these novel sulfide and sulfone derivatives were screened for their antibacterial and antifungal activities against various microorganisms. [ABSTRACT FROM AUTHOR]

In the title molecule, C7H6N4O3, the bicyclic ring system is planar with the carboxymethyl group inclined by 81.05 (5)⋅ to this plane. In the crystal, corrugated layers parallel to (010) are generated by N--H⋅ ⋅ ⋅O, O--H⋅ ⋅ ⋅N and C--H⋅ ⋅ ⋅O hydrogen-bonding interactions. The layers are associated through C--H⋅ ⋅ ⋅⋅(ring) interactions. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋅ ⋅ ⋅O/O⋅ ⋅ ⋅H (34.8%), H⋅ ⋅ ⋅N/N⋅ ⋅ ⋅H (19.3%) and H⋅ ⋅ ⋅H (18.1%) interactions. The volume of the crystal voids and the percentage of free space were calculated to be 176.30 A ° 3 and 10.94%, showing that there is no large cavity in the crystal packing. Computational methods revealed O--H⋅ ⋅ ⋅N, N--H⋅ ⋅ ⋅O and C--H⋅ ⋅ ⋅O hydrogen-bonding energies of 76.3, 55.2, 32.8 and 19.1 kJ mol1, respectively. Evaluations of the electrostatic, dispersion and total energy frameworks indicate that the stabilization is dominated via dispersion energy contributions. Moreover, the optimized molecular structure, using density functional theory (DFT) at the B3LYP/6-311G(d, p) level, was compared with the experimentally determined one. The HOMO-LUMO energy gap was determined and the molecular electrostatic potential (MEP) surface was calculated at the B3LYP/6-31G level to predict sites for electrophilic and nucleophilic attacks. [ABSTRACT FROM AUTHOR]

Novel 2-heteroaryl-N-[4-(substituted aryl)thiazol-2-yl]propanamide derivatives (7a–7o) were synthesized and investigated for their antimicrobial activity. Among the tested compounds, 2-[(1H-Benzimidazol-2-yl)thio]-N-[4-(naphthalen-2-yl)thiazol-2-yl]propanamide (7e) and N-[4-(4-Chlorophenyl)thiazol-2-yl]-2-[(1-methyl-1H-tetrazol-5-yl)thio]propanamide (7f) showed the highest antibacterial activity, whereas 2-[Benzothiazol-2-ylthio]-N-[4-(4-chlorophenyl)thiazol-2-yl]propanamide (7i) and 2-[(1H-Benzimidazol-2-yl)thio]-N-[4-(4-chlorophenyl)thiazol-2-yl]propanamide (7j) displayed anticandidal effect against C. parapsilosis and C. glabrata. The cytotoxic activity of the compounds (7a–7o) was also tested against HL-60 human leukemia cells, THP-1 human monocytic leukemia cells, and NIH/3T3 mouse embryonic fibroblast cells. Compound N-[4-(4-Chlorophenyl)thiazol-2-yl]-2-[(1-methyl-1H-imidazol-2-yl)thio]propanamide (7 g) and compound 7j exhibited high cytotoxicity against HL-60; and compounds 2-[(1-Methyl-1H-imidazol-2-yl)thio]-N-[4-(naphthalen-2-yl)thiazol-2-yl]propanamide (7b), 7 g and N-[4-(4-Methoxyphenyl)thiazol-2-yl]-2-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]propanamide (7 m) also had cytotoxic activity against THP-1 compared with standard drug with selective profile. Additionally, in silico physicochemical properties of the compounds were described. [ABSTRACT FROM AUTHOR]

Thiazolo[3,2-a]pyrimidines namely ethyl 2-acetyl-5-(2-fluorophenyl)-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate 3a, ethyl 2-acetyl-5-(3-fluorophenyl)-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate 3b, and ethyl 2-acetyl-5-(4-fluorophenyl)-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate 3c were obtained by one pot synthesis using substituted 3,4 dihydropyrimidine2-thione (1a–1c) and 3-chloro-2,4-pentanedione in ethanol and characterized by single-crystal X-ray diffraction. The variation in the position of fluorine atom on pyrimidine nucleus and insight into the self-assembly of compounds with varied types of non-covalent interactions has great influence on crystal packing. [ABSTRACT FROM AUTHOR]

Thiophenes are a highly important group of heterocycles and have been of great interest to researchers due to their various reactivities. Many synthetic strategies are used to generate functionalized thiophene derivatives. Several reactions are described, depending on the reactivity of the substituents attached to the thiophene nucleus toward different nucleophiles to yield the versatile thiophene products. Many diverse applications have been utilized for thiophenes from medicinal chemistry to material science. [ABSTRACT FROM AUTHOR]

Three title compounds, namely, 2-(4-chlorobenzyl)-5-[(1H-indol-3-yl)methyl]-6- phenylimidazo[2,1-b][1,3,4]thiadiazole, C26H19ClN4S, (I), 2-(4-chlorobenzyl)-6- (4-fluorophenyl)-5-[(1H-indol-3-yl)methyl]imidazo[2,1-b][1,3,4]thiadiazole, C26H18ClFN4S, (II), and 6-(4-bromophenyl)-2-(4-chlorobenzyl)-5-[(1H-indol-3- yl)methyl]imidazo[2,1-b][1,3,4]thiadiazole, C26H18BrClN4S, (III), have been prepared using a reductive condensation of indole with the corresponding 6-aryl-2-(4-chlorobenzyl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehydes (aryl = phenyl, 4-fluorophenyl or 4-bromophenyl), and their crystal structures have been determined. The asymmetric unit of compound (I) consists of two independent molecules and one of the molecules exhibits disorder of the 4-chlorobenzyl substituent with occupancies 0.6289 (17) and 0.3711 (17). Each type of molecule forms a C(8) chain motif built from N--H ⋯ N hydrogen bonds, which for the fully ordered molecule is reinforced by C--H ⋯ π interactions. In compound (II), the chlorobenzyl unit is again disordered, with occupancies 0.822 (6) and 0.178 (6), and the molecules form C(8) chains similar to those in (I), reinforced by C--H ⋯ π interactions involving only the major disorder component. The chlorobenzyl unit in compound (III) is also disordered with occupancies of 0.839 (5) and 0.161 (5). The molecules are linked by a combination of one N--H ⋯ N hydrogen bond and four C--H⋯π interactions, forming a three-dimensional framework. [ABSTRACT FROM AUTHOR]

A novel series of bis- and poly(arydiazenyl)thiazoles were prepared in good yields by the reaction of the appropriate α-keto-hydrazonoyl chlorides with the corresponding bis- and poly(hydrazinecarbothioamide) in refluxing EtOH/DMF in the presence of few drops of TEA. Based on elemental analyses as well as spectral data, the structures of the new compounds were confirmed. [ABSTRACT FROM AUTHOR]

A novel series of bis(thiazolylchromen‐2‐one) derivatives 8 were prepared in good yields by the reaction of the appropriate bis(α‐bromoketones) 7 with 2‐(1‐(2‐oxo‐2H‐chromen‐3‐yl)ethylidene) hydrazinecarbothioamide (6) in refluxing EtOH in the presence of few drops of TEA. Some other isomeric derivatives of bis(thiazolylchromen‐2‐one) 11 and 13 were also successfully obtained by the reaction of bromoacetylcoumarin 9 with the corresponding bis(ethan‐1‐yl‐1‐ylidene))bis(hydrazinecarbothioamides) 10 and 12. The structures of the new compounds were established based on elemental analyses as well as spectral data. [ABSTRACT FROM AUTHOR]

The reaction of diethyl chloroethynylphosphonate with methyl (ethyl) 6-methyl-4-aryl-2-thio-1,2,3,4-tetrahydropyrimidine-5-carboxylate proceeded through the replacement of the chlorine atom and subsequent intramolecular cyclization to yield methyl (ethyl) 3-(diethoxyphosphoryl)-5-aryl-7-methyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylates. [ABSTRACT FROM AUTHOR]

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