Ring Transformation of a 2(3H)‐furanone Derivative into Oxazinone and Pyrimidinone Heterocycles

Abstract

The conversion of the 2(3H)‐furanone into the oxazinone and pyrimidinone derivatives is studied. A 2‐(furan‐2‐ylmethylene)‐4‐oxo‐4‐phenylbutanoyl azide 3 was synthesized to carry out these conversions through its thermolysis in dry benzene and/or base‐catalyzed decomposition of this azide in the presence of different amines. The structures of all compounds were demonstrated from their spectral data and elemental analyses.

Synthesis, computational chemical study, antiproliferative activity screening, and molecular docking of some thiophene-based oxadiazole, triazole, and thiazolidinone derivatives

“…1 H NMR (d, ppm): 7.95-7.41 (m, 8H, Ar-H), 4.90 (s, 2H, CH 2 ), 4.15 (q, 2H, CH 3 CH 2 , J = 6.5 Hz), 1.21 (t, 3H, CH 2 CH 3 , J = 6.5 Hz). EIMS, m/z, (%): 345.41 (M + , 37), 272.30 (M + − COOC 2 H 5 , 49), 186.42 (26), 135.03 (23), 110.21 (30) N 0 -Dodecanoylthiophene-2-carbohydrazide (7). 44 A solution of thiophene-2-carbohydrazide 1 (1 mmol) and dodecanoyl chloride (1.1 mmol) in pyridine (5 mL) was heated in a water bath at ∼90 °C for 6 h. The reaction mixture was cooled to room temperature and then poured onto ice/HCl while stirring.…”

“…On the other hand, the acid hydrazides have been easily converted into hydrazones, oxadiazoles, triazoles, and various heterocycles. [7][8][9][10] Among the hydrazides, 2-thienohydrazides have received extensive attention due to the biological effects of thiophene moiety which were recognized and practically applied in herbicides, 11 fungicides, 12 and several agents. 13 Otherwise, it was shown that thiosemicarbazide derivatives provide various functionality through nucleophilic and electrophilic centers.…”

Synthesis, SAR studies, and insecticidal activities of certain N-heterocycles derived from 3-((2-chloroquinolin-3-yl)methylene)-5-phenylfuran-2(3H)-one against Culex pipiens L. larvae

“…[1][2][3][4][5][6][7][8][9][10][11][12][13] Accordingly, furanones are found to be easily converted to a variety of heterocyclic skeletons of biological importance. [14][15][16][17][18][19][20] A broad range of pharmacological activities including insecticidal, antiviral, anticancer, antimicrobial, antimalarial, anti-inammatory, and analgesic properties have been documented in quinoline (benzo[b]pyridine) derivatives (Fig. 1).…”

Evaluation of some new heterocycles bearing 2‐oxoquinolyl moiety as immunomodulator against highly pathogenic avian influenza virus (H5N8)

“…These products have low toxicity in their application [7]. In turn, furan‐2(3 H )‐ones are of considerable interest as they are versatile key materials for synthesis of a variety of heterocycles having a diverse of pharmacological applications [8–18]. Furthermore, quinolin‐2(1 H )‐ones are of fascinating interest according to their role in natural products and their pharmacological effects [19–27].…”