Synthesis of Triazole and Isoxazole Based Novel Unsymmetrical Bis‐heterocycles

Pd-Catalysed [3 + 2]-cycloaddition towards the generation of bioactive bis-heterocycles/identification of COX-2 inhibitors via in silico analysis

“…In recent years the attention of the scientific community has been increasingly drawn towards the development of bis-heterocycles owing to their immense biological attributes. 1 Bis-heterocycles containing dihydroisoxazoles and cyclic carbonates are a new class of organic molecules which may exhibit the synergistic bioactivity of individual rings. These are privileged scaffolds found in natural products (acivicin, (+)-calafianine) and other pharmaceuticals (Fig.…”

Solvent- and Catalyst-Free One-Pot Green Bound-Type Fused Bis-Heterocycles Synthesis via Groebke–Blackburn–Bienaymé Reaction/SNAr/Ring-Chain Azido-Tautomerization Strategy

“…2-Aminothiazoles were purchased from Sigma-Aldrich and used without further purification. 1 H and 13 C NMR spectra were acquired on Bruker ADVANCE III spectrometers (500 MHz) at 295 K in CDCl 3 . Chemical shifts are reported in parts per million (δ/ppm).…”

“…Bis-heterocycles are molecules that can be formed by two linked, bound, spacer, or fused heterocyclic scaffolds. The purpose behind the combination of two heterocycles is to improve their potential applications in different areas such as chelating agents and metal ligands, complexes or metal–organic framework precursors, as well as electrical materials, and mainly in the development of bioactive molecules and drugs. − In this context, tetrazolo­[1,5- a ]­quinolines − and imidazo­[2,1- b ]­thiazoles are important fused heterocycles that exhibit a wide variety of biological activities. For example, imidazo­[2,1- b ]­thiazole I demonstrated to be a potent antidiabetic, benzo­[ d ]­imidazo­[2,1- b ]­thiazole II displayed a strong antifungal activity compared to standard fluconazole, and compound III showed an antibacterial activity comparable to that of ampicillin (Figure ).…”

“…FT-IR (ATR) ν max /cm −1 : 3253, 1570, 1549, 1294;1 H NMR (400 MHz; CDCl 3 ; 25 °C; TMS): δ 8.47 (s, 1H), 8.15 (dd, J = 7.2, 4.0 Hz, 1H), 8.07 (d, J = 6.8 Hz, 1H), 7.89 (d, J = 6.4 Hz, 1H), 7.77 (ddd, J = 6.8, 5.6, 1.2 Hz, 1H), 7.60 (ddd, J = 6.8, 5.6, 1.2 Hz, 1H), 7.42 (dd, J = 6.4, 2.0 Hz, 1H), 7.19 (ddd, J = 7.2, 6.8, 2.0 Hz, 1H), 3.41−3.39 (m, 1H), 2.75 (br s, 1H), 1.80−1.77 (m, 2H), 1.58−1.55 (m, 2H), 1.46− 1.44 (m, 1H), 1.08−1.01 (m, 4H); 13 C NMR (100 MHz, CDCl 3 ; 25 °C; TMS): δ 160.8, 158.9, 149.0, 147.4, 143.6, 140.6, 134.4, 131.9, 131.0 (d, J = 207.9 Hz), 130.8, 128.6, 128.4, 128.0, 127.6, 127.5, 115.2 (d, J = 7.0 Hz), 113.8 (d, J = 19.2 Hz), 111.2 (d, J = 21.6 Hz), 57.5, 33.8 (2C), 25.8, 24.8 (2C); HRMS (ESI + ) m/z: calcd for C 24 H 21 N 7 SF + , 458.1558; found, 458.1560. CDCl 3 ; 25 °C; TMS): δ 160.8, 158.9, 146.4, 145.1, 133.8, 133.7, 132.8 (d, J = 204.9 Hz), 130.6, 130.1, 129.8, 129.3, 128.5, 124.9, 121.1, 116.9, 116.7 (d, J = 6.9 Hz), 113.5 (d, J = 19.5 Hz), 111.1 (d, J = 21.6 Hz), 55.0, 29.3 (3C); HRMS (ESI + ) m/z: calcd for C 22 H 19 N 7 SF + , 432.1401; found, 432.1405.…”

<strong>Synthesis of <em>bis</em>-heterocycles type spacer containing 1,5-disubstituted-1<em>H</em>-tetrazoles</strong>

“…Recently, the efficient synthesis of bis-heterocycles has gained more attention due to their plethora of applications in the field of: organic synthesis, optics, materials, polymer sciences, agrochemistry, and particularly medicinal chemistry [1]. Two heterocyclic moieties with the similar or different biological activity can be suitably placed to synthesize complex molecules with potential application in the field of medicinal chemistry [2][3][4].…”