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3-(Benzofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde was used, as a precursor for the synthesis of a series of novel heterocycles by facile reactions with 3-oxo-3-phenylpropanenitrile, 2-cyanoethanethioamide, and various hydrazides such as cyanoacetohydrazide, acetohydrazide, and carbohydrazide derivatives. The structures of the products were confirmed by various spectroscopic methods along with the X-ray crystal structures.

This review deals with the methods for the synthesis of various bicyclic pyrimidothiazines which are not annelated with other cycles. Syntheses of pyrimido[2,1-b]-, pyrimido[4,5-b]-, pyrimido[5,4-e...

Series of novel 1,2-bis((3-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazines 4 and 2-(5-(3-(1,2,3-triazol-4-yl)pyrazol-4-yl) pyrazol-1-yl)thiazoles 13 were synthesized using simple and convenient procedures, and their structures were established. Treatment of pyrazole-4-carbaldehydes 1 with methyl ketones in alkaline medium gave the corresponding (E)-1-aryl-3-(3-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-ones 3 in 82–86% yields. Treatment of 3 with hydrazine hydrate gave 4, in 69–75% yields, rather than the expected 1-aryl-5-methyl-4-(1-aryl-4-(3-phenyl-4,5-dihydro-1H-pyrazol-5-yl)-1H-pyrazol-3-yl)-1H-1,2,3-triazoles. Reactions of 3 with thiosemicarbazide gave the corresponding carbothioamides 9 which in reaction with phenacyl bromides gave the corresponding dihydropyrazolylthiazoles 13 in 82–87% yields. The novel synthesized product exhibits good antimicrobial activities against the tested microorganisms.

C18H17N5O2, monoclinic, P21/n (no. 14), a = 20.3702(7) Å, b = 7.3482(2) Å, c = 23.2504(10) Å, β = 106.507(4)°, V = 3336.8(2) Å3, Z = 8, R gt(F) = 0.0571, wR ref(F 2) = 0.1507, T = 296(2) K.

C27H23F2N3S, 0.5(C3H7NO), monoclinic, C2/c (no. 15), a = 25.1579(10) Å, b = 9.9356(4) Å, c = 20.1799(7) Å, β = 91.741(4)°, V = 5041.8(3) Å3, Z = 8, R gt(F) = 0.0508, wR ref(F 2) = 0.1385, T = 296(2) K.

C22H22N8O2, monoclinic, P21/c (no. 14), a = 15.5175(5) Å, b = 7.9715(3) Å, c = 17.3941(5) Å, β = 90.005(3)°, V = 2151.61(12) Å3, Z = 4, R gt(F) = 0.0592, wR ref(F 2) = 0.1780, T = 293(2) K.

The title molecule, C22H21FN8O, comprises fluorophenyl (A), methyltriazolyl (B), methyltriazolyl (C) and tolyl (D) rings. The twist angles between the planes through neighbouring ring pairs A/B, B/C and C/D are 45.0 (1), 9.4 (1) and 43.2 (1)°, respectively. Intermolecular π–π interactions between rings A and C and between B and D propagate the structure in the [010] direction and weak C—H...O interactions also occur.

The title molecule, C25H17ClFN3S, contains indenothiazolyl (A), pyrazolyl (B), fluorophenyl (C) and chlorophenyl (D) groups. The dihedral angles between the ring planes A/B, B/C and B/D are 14.2 (1), 83.0 (1) and 6.5 (2)°, respectively. In the crystal, pairs of molecules related by inversion symmetry are linked by pairwise weak C—H...N interactions, forming dimers. These dimers interact through π–π contacts between the thiazolyl units [centroid-to-centroid distance = 3.826 (1) Å], forming chains along [010].

The asymmetric unit of the title compound, C20H17N5O, consists of two independent molecules. The molecules comprise tolyl (A), triazolyl (B), pyrazolecarbaldehydyl (C) and phenyl (D) groups. The angles between the planes through neighouring rings A/B, B/C and C/D are 39.1 (1), 6.0 (1) and 12.6 (1)°, respectively, for the first molecule and 46.0 (1), 4.6 (1) and 8.5 (2)°, respectively, for the second. In the crystal, the two independent molecules form dimers linked by four C—H...O hydrogen bonds with each O atom accepting two such links.

The title compound, C27H17ClFN3O2S, comprises chromonyl (A), thiazolyl (B), pyrazolyl (C), chlorophenyl (D) and fluorophenyl (E) rings with twist angles between the planes of adjacent rings pairs A/B, B/C, C/D and C/E of 14.1 (1), 18.2 (2), 1.3 (1) and 4.9 (1)°, respectively. The crystal structure is characterized by a range of intermolecular interactions including C—H...F, C—H...Cl and C—H...O contacts. Aromatic π–π stacking between chromonyl groups and chlorophenyl groups [centroid–centroid separations = 3.7170 (16) and 4.017 (2) Å, respectively] lead to columns of molecules propagating parallel to the [100] direction.

The title compound, C23H17ClFN5OS, comprises fluorophenyl (A), furanyl (B), pyrazolyl (C), methylthiazoyl (D) and chlorophenyl (E) rings. The B–C–D–E linked ring system is close to planar with the dihedral angles B/C, C/D and D/E being 7.6 (1), 3.4 (1) and 8.4 (1)°, respectively. The fluorophenyl group is almost perpendicular to the pyrazoyl ring, as indicated by an A/C twist angle of 79.4 (1)°. In the crystal, inversion dimers linked by pairs of C—H...S contacts are observed.

The title compound, C28H23FN6S, comprises phenyl (A), triazolyl (B), thiazolyl (C), pyrazoyl (D), tolyl (E) and fluorophenyl (F) rings, with twist angles between neighbouring rings pairs A/B, B/C, C/D, D/E and D/F of 64.6 (1), 11.7 (2), 23.5 (2), 8.2 (2) and 73.3 (1)°, respectively. A short intramolecular C—H...N contact and a weak intermolecular C—H...π interaction occur. The crystal chosen for data collection was found to be an inversion twin.

The current review article represents a survey of the literature covering the strategies for the synthesis of thiadiazolotriazines for the first time. The review is divided according to the type of...

Thiazoloquinazoline scaffold constitutes a promising source of inspiration for the synthesis of novel bioactive molecules. The current review article summarizes the most recent synthetic routes toward thiazoloquinazoline derivatives, published between the years 1983 and 2016. According to the position of fusion between thiazole and quinazoline rings, the thiazoloquinazoline derivatives in this review were classified into seven major types.

Several structural types of thiazoloindoles can be distinguished with regard to the position of the fusion between the thiazole, benzene, and pyrrole rings. The present review describes the synthet...

This review article presents the available synthetic routes for the preparation of different types of imidazothiazines. Imidazothiazines dealt with are classified into five types based on the posit...

C23H17F2N5OS, monoclinic, P21/c (no. 14), a = 5.2272(4) Å, b = 26.7398(15) Å, c = 15.2645(10) Å, β = 97.726(7)°, V = 2114.2(2) Å3, Z = 4, R gt(F) = 0.0547, wR ref(F 2) = 0.1371, T = 296(2) K.

C23H16ClN5S, monoclinic, P21/n (no. 14), a = 19.8348(9) Å, b = 8.8376(3) Å, c = 23.8486(10) Å, β = 97.646(4)°, V = 4143.3(3) Å3, Z = 8, R gt(F) = 0.0492, wR ref(F 2) = 0.1276, T = 293(2) K.

In the title solvate, C28H20ClN7O2S·C3H7NO, the main molecule consists of chlorophenyl (A), thiadiazolyl (B), pyrazolyl (C), phenyl (D) and indolyl (E) rings, with twist angles between neighbouring rings A/B, B/C, C/D and D/E of 32.6 (1), 14.8 (1), 60.8 (1) and 20.1 (1)°, respectively. The dimethylformamide solvent molecule accepts an N—H...O hydrogen bond from the indole group. In the extended structure, molecules related by 21 screw axes are stacked in the [001] direction to form columns linked by weak C—H...O interactions.

The title compound, C17H11ClN4O2, consists of chlorophenyl (A), isoxazolyl (B), oxadiazolyl (C) and phenyl (D) rings with twist angles between the planes through neighbouring rings A/B, B/C and C/D of 14.9 (1), 1.8 (1) and 8.9 (1)° respectively. In the crystal, adjacent molecules related by inversion symmetry form columns parallel to the [010] direction through π–π stacking [shortest centroid–centroid separation = 3.6203 (10) Å]; these are cross-linked by N—H...N interactions in the [001] direction.

The asymmetric unit of the title compound, 2C20H17BrN6S·C3H7NO, comprises two molecules of the thiazole derivative and one molecule of dimethylformamide (DMF) solvent. The twist angles between the planes through the bromophenyl, methylthiazolyl and indolyl groups are 10.1 (1) and 44.2 (1)°, respectively, for one molecule and 11.3 (1) and 1.6 (1)° for the other. In the crystal, N—H...N hydrogen bonds link four of the main molecules into tetramers. N—H...O bonds involving the DMF solvent molecule also occur.

In the title hydrate, C17H18N6O·H2O, the twist angles between the least-squares planes of the pyrolyl/methyltriazolyl/tolyl groups are 11.4 (2) and 7.9 (1)°, respectively. In the crystal, centrosymmetric tetramers (two organic molecules and two water molecules) are linked by N—H...O and O—H...O hydrogen bonds. Weak aromatic π–π stacking interactions between the triazolyl rings [centroid–centroid separation = 3.6422 (10) Å] link the tetramers.

The conformation of the title compound, C25H24N4O3S, is influenced by an intramolecular N—H...O hydrogen bond, which generates an S(6) ring. The twist angles between the planes through the toluyl, methyltriazole, thiophene and phenyl rings are 60.1 (1), 33.5 (1) and 39.9 (1)°, respectively. In the crystal, molecules are stacked along the a-axis direction with weak aromatic π–π stacking interactions occurring between the thiophene rings [centroid-to-centroid distance = 3.7285 (15) Å].

The asymmetric unit of the title compound, C17H13N5O, comprises four independent molecules (A–D). The respective interplanar angles between the phenyl/oxadiazole/methyltriazole/phenyl rings for the four independent molecules are A 8.8 (2), 13.0 (2), 22.5 (2)°; B 6.3 (2), 8.9 (2), 29.0 (1)°; C 4.0 (2), 10.0 (2), 24.5 (2)°; D 3.5 (2), 10.1 (2), 27.2 (2)°. In the crystal, molecules form two separate stacks parallel to the b-axis direction: one consists of A and D molecules, and the other of B and C molecules. Aromatic π–π stacking is observed within each stack, with the shortest centroid–centroid separation being 3.552 (2) Å.

The title compound, C19H16N4O3, crystallizes with two molecules (A and B) in the asymmetric unit. In molecule A, the dihedral angles between the triazole ring and the toluyl and nitrobenzene rings are 62.68 (16) and 10.77 (15)°, respectively. The corresponding data for molecule B are 68.61 (17) and 15.59 (15)°, respectively. In the crystal, the B molecules are linked by C—H...N hydrogen bonds to generate [001] chains. Weak C—H...π(benzene) and N—O...π(triazole) contacts are also present.

In the title compound, C24H22N4O2S, the dihedral angle between the triazole and thiophene rings is 4.83 (14)°. The dihedral angles between the triazole and tolyl rings and between the thiophene and phenyl rings are 48.42 (16) and 9.23 (13)°, respectively. An intramolecular N—H...O hydrogen bond closes anS(6) loop. In the crystal, molecules are stacked parallel to thea-axis direction with weak π–π interactions between adjacent thiophenyl and triazolyl groups within the stack [centroid–centroid separation = 3.9811 (16) Å].

The asymmetric unit of the title compound, C20H18N8O2, comprises one complete molecule and a half molecule completed by crystallographic twofold symmetry leading toZ= 12. The dihedral angles between the planes of the linked phenyl and methyltriazolyl groups are 69.48 (5) and 44.85 (9)° for the first molecule and 42.88 (9)° for the second. The conformations of the diformyl hydrazyl groups of the molecules are similar as indicated by C—N—N—C torsion angles of −83.4 (2) and −86.4 (3)°. In the crystal, neighbouring molecules are linked by pairs of N—H...O hydrogen bonds to form independent columns propagating parallel to thec-axis direction.

The asymmetric unit of the title compound, C37H28BrClN8S, comprises one mol­ecule. The mol­ecule consists of two ring systems joined by a C—C bond between the di­hydro­pyrazolyl and pyrazolyl rings of the two extended ring systems. The angles between adjacent ring planes of the tol­yl–triazol­yl–pyrazol­yl–phenyl ring system are 48.2 (1), 12.3 (2) and 22.2 (2)°, respectively, with angles of 19.7 (1), 5.6 (2) and 0.9 (2)° between the rings of the chloro­phen­yl–thia­zol­yl–di­hydro­pyrazol­yl–bromo­phenyl set. The pyrazolyl and di­hydro­pyrazolyl rings are inclined at 68.3 (1)° to one another. In the crystal, C—H⋯Cl inter­actions form chains of mol­ecules parallel to the b-axis direction.

In this paper we present the synthesis of a novel series of 3-(5-methyl-1-aryl-1 H -1,2,3-triazol-4-yl)-1-phenyl-1 H -pyrazoles 3-6 by employing Vilsmeier-Haack reaction followed by Knoevenagel condensation on 1-aryl-3-acetyl-4-methyl-1,2,3-triazoles 1a,b. The cytotoxicity and in vitro anticancer evaluation of the prepared compounds have been assessed against four different human cancer cell lines including breast MCF-7; liver HepG2 and lung cancer A549 as well as human normal melanocyte HFB4. The results revealed that the prepared compounds exert their actions in MCF-7 and HepG2. Compounds 4a and 6a revealed promising anticancer activity compared to the activity of the commonly used anticancer drug, doxorubicin. MCF-7 cells are slightly more sensitive to the tested compounds than HepG2 cells.

C29H25FN6S, triclinic, P1̅, a = 7.5726(8) Å, b = 11.1428(13) Å, c = 16.412(2) Å, α = 91.823(5)°, β = 102.277(5)°, γ = 106.692(4)°, V = 1289.8(3) Å3, Z = 2, Rgt(F) = 0.079, wRref(F2) = 0.205, T = 296 K.

The asymmetric unit of the title solvate, C17H16N8S2·0.25C3H7NO, consists of two C17H16N8S2 molecules and a dimethylformamide molecule disordered about a crystallographic inversion centre. Both triazole molecules feature an intramolecular C—H...N interaction, which generates an S(6) ring in each case. In the crystal, the components are linked by N—H...N and N—H...S hydrogen bonds to form [001] chains, which are cross-linked by weak C—H...O, C—H...N and C—H...S interactions.

In the title compound, C15H16N4O3S, the dihedral angle between the aromatic rings is 15.90 (19)°. The molecule features two intramolecular N—H...O hydrogen bonds, which both close S(6) rings. In the crystal, weak C—H...O interactions link the molecules into [010] chains.

The asymmetric unit of the title compound, C18H13F2N3O, comprises two molecules with similar conformations. In the crystal, weak C—H...F interactions form chains of molecules and the chains are stacked to form layers parallel to (101).

The non-H atoms of the title molecule, C19H16N2O2, are almost coplanar (r.m.s. deviation = 0.019 Å), apart from the phenyl group, which is disordered with two components of almost equal occupancy: the dihedral angle between them is 78.9 (3)°. In the crystal, weak C—H...N hydrogen bonds link the molecules into [001] chains and aromatic π–π stacking interactions [shortest centroid–centroid separation = 3.747 (2) Å] form columns parallel to the c-axis direction.

The title compound, C13H9NO4, is almost planar (r.m.s. deviation = 0.071 Å). In the crystal, weak C—H...O and C—H...N interactions connect the molecules into ribbons propagating parallel to thea-axis direction.

In the title compound, C12H13N3O, thep-tolyl ring is twisted away from the mean plane (r.m.s. deviation = 0.044 Å) of the rest of the molecule by 50.84 (6)°. In the crystal, molecules are linked by C—H...π interactions, forming zigzag chains propagating in theb-axis direction.

The current review deals with the use of ring expansion reactions for the synthesis of sulfur-containing heterocycles. Ring enlargement offers by far a convenient method for the synthesis of ‘medium-sized ring systems’, which are usually difficult to obtain or even produced in low yields. These reactions are often catalytically processed starting from a single cyclic precursor and, therefore, are superior to alternative classical iterative synthetic approaches in terms of atomic and conversion efficiency. The current review aims to shed light on the synthetic approaches that exist to afford medium-sized sulfur heterocycles from preexisting smaller rings (e.g., three-, four-, five-, six- and seven-membered rings).

C29H23N7O, triclinic, P1̅ (no. 2), a = 8.2785(12) Å, b = 12.1750(18) Å, c = 13.8122(16) Å, α = 114.401(13)°, β = 103.083(11)°, γ = 93.384(12)°, V = 1216.5(3)Å3, Z = 2, R gt(F) = 0.0713, wR ref(F 2) = 0.1880, T = 293(2) K.

2-Substituted benzimidazoles 3a-c was prepared via condensation of ethyl pyruvates 2a-c with 2-phenylenediamine in glacial acetic acid. Pyrrolo[1,2- a ]benzimidazole derivatives 5 and 8 were prepared via cyclocondensation of compounds 3a,b with phosphorus oxychloride or acetic anhydride in presence of sodium acetate respectively. Reactivity of pyruvate 2 towards 2-aminophenol, hydroxylamine and cyanothioacetamide was also investigated. They exhibited potent antimicrobial activity comparable to clinical drugs such as ciprofloxacin and ketoconazole. Compounds 3a , 11 and 13 showed excellent antimicrobial activity against all the tested microbes, and Compound 11 showed lower MIC values against all the tested organisms.

Ethyl coumarin-3-carboxylate occupies an important position in the organic synthesis and is used in production of biologically active compounds. Thus, the data published over the last few years on the methods of synthesis and chemical properties of ethyl coumarin-3-carboxylate are reviewed here for the first time. The reactions were classified as coumarin ring reactions and ester group reactions, and some of these reactions have been applied successfully to the synthesis of biologically and industrially important compounds.

C13H11N3O2, triclinic, P1̄ (no. 2), a = 7.889(2) Å, b = 9.367(3) Å, c = 9.630(3) Å, α = 64.82(3)°, β = 106.507(4)°, γ = 84.57(2), V = 585.1(3) Å3, Z = 2, R gt(F) = 0.0550, wR ref(F 2) = 0.1455, T = 293(2) K.

C24H23N5O3S, triclinic, P1̅ (no. 2), a = 9.1704(9) Å, b = 10.1253(11) Å, c = 12.2182(14) Å, α = 83.686(10)°, β = 89.542(9)°, γ = 76.982(9)°, V = 1098.5(2) Å3, Z = 2, R gt(F) = 0.0551, wR ref(F 2) = 0.1510, T = 296(2) K.

C31H26N8O, triclinic, P1̄ (no. 2), a = 6.6046(3) Å, b = 15.1056(8) Å, c = 15.2115(8) Å, α = 61.996(2)°, β = 80.390(3)°, γ = 87.579(2)°, V = 1319.97(12) Å3, Z = 2, R int = 0.108, wR(F 2) = 0.143, T = 296(2) K.

C20H17N5O, triclinic, P1̅ (no. 2), a = 11.5358(7) Å, b = 13.8746(9) Å, c = 16.3942(10) Å, α = 85.958(5)°, β = 87.407(5)°, γ = 87.619(5)°, V = 2612.8(3)Å3, Z = 6, R gt(F) = 0.0607, wR ref(F 2) = 0.1510, T = 293(2) K.

C23H17ClFN5S2, monoclinic, P21/c (no. 14), a = 20.9691(12) Å, b = 11.5316(6) Å, c = 9.2546(4) Å, β = 95.484(4)°, V = 2227.6(2) Å3, Z = 4, R gt(F) = 0.0468, wR ref(F 2) = 0.1126, T = 296 K.

C28H20FN3OS, triclinic, P1̅ (no. 2), a = 9.5719(5) Å, b = 10.7499(6) Å, c = 10.9238(5) Å, α = 95.470(4)°, β = 102.133(4)°, γ = 97.962(4)°, V = 1079.30(10) Å3, R gt(F) = 0.0482, wR ref(F 2) = 0.1143, T = 150(2) K.