Efficient synthesis of acridinediones in aqueous media

Abstract

Commercially available dimedone, benzaldehydes and ammonium acetate from Spectrochem were used. Progress of reactions was monitored by thin layer chromatography (TLC). NMR spectra were recorded in CDCl 3 at 300 MHz for 1 H and 75 MHz for 13 C on Bruker Avance DPX-300MHz. Chemical shifts were reported in δ (ppm) relative to CDCl 3 ( 13 C) as internal standards. Integrals are in accordance with assignments, coupling constants are given in Hz.The HRMS was recorded on a JOEL-AccuTOF JMS-T100LC Mass spectrometer having a DART source. The IR spectra were recorded on Spectrum RX-1 FTIR, Perkin Elmer. Yields refer to quantities obtained after chromatography. Melting point of compounds were recorded on LABINDIA make melting point apparatus and are uncorrected. General experimental procedure Synthesis of 3-amino-5,5-dimethylcyclohex-2-enone (2):A mixture of dimedone (1) (1.0 g, 7.1 mmol) and NH 4 OAc (1.32 g, 21.4 mmol) was heated in 30 mL of water at 80 ᴏ C for 5 hours. After the TLC indicated the consumption of dimedone (2), the reaction mixture was extracted with ethyl acetate several times. The combined organic layer was dried over sodium sulphate and evaporated to provide enaminone (2) (0.9 g, 90%) as light yellow solid.

Synthesis of 1,8-Dioxo-decahydroacridine Derivatives via Ru-Catalyzed Acceptorless Dehydrogenative Multicomponent Reaction

“…It was obtained as a yellow solid . Column chromatography (hexane:ethylacetate = 50:50 with 1% NEt 3 ).…”

Photocatalytic C–H Thiocyanation of NH2-Enaminones and the Tunable Synthetic Routes to 2-Aminothiazoles and 2-Thiazolinones

“…■ EXPERIMENTAL SECTION General Experimental Information. Enaminones 1a−1w, 14 enaminone 1x, 15 and enaminoester 1y 14e were synthesized following literature processes at a 10 mmol scale (characterization data and 1 H/ 13 C NMR spectra for new compounds are provided in the Supporting Information). All other chemicals and solvents used in the experiments were obtained from commercial sources and used directly without further purification.…”

Application of Cyclohexane‐1,3‐diones in the Synthesis of Six‐Membered Nitrogen‐Containing Heterocycles

“…Environmentally benign catalyst‐free approaches have been also developed for the synthesis of acridine‐1,8‐dione derivatives [187–189] . In 2020, a metal‐free method has developed where glycerol (the low‐cost side product of biodiesel industries) used as a solvent and catalyst at 65 °C for acridine‐1,8‐dione derivatives 36 & 37 synthesis with good to excellent yield (Scheme 31).…”

“…[186] Environmentally benign catalyst-free approaches have been also developed for the synthesis of acridine-1,8-dione derivatives. [187][188][189] In 2020, a metal-free method has developed where glycerol (the low-cost side product of biodiesel industries) used as a solvent and catalyst at 65 °C for acridine-1,8dione derivatives 36&37 synthesis with good to excellent yield (Scheme 31). [68] In the same year, a similar reaction reported utilizing glycerol as solvent and catalyst but the reaction was carried out at room temperature.…”