One‐pot Synthesis ofN‐Hydroxylacridine Derivatives in Water

Abstract

N‐Hydroxylacridinedione derivatives were synthesized by three‐component reaction of aromatic aldehydes, 1,3‐dicarbonyl compounds and hydroxylamine hydrochloride using triethylbenzylammonium chloride (TEBA) as the catalysis in water. The reaction has many advantages including good yields, easy to be separated and environmental friendliness.

AN ECO-FRIENDLY ONE-POT SYNTHESIS OF 4,4'-(ARYLMETHYLENE)BIS(1H-PYRAZOL-5-OLS) USING [Et3NH][HSO4] AS A RECYCLABLE CATALYST

“…The results showed that reactions in solvents take more time and also the yields are low compared to the solvent-free conditions (Table 1, entries [13][14][15][16][17][18]. Water has been identified as an ideal solvent because it is abundant, inexpensive, non-flammable and environmentally benign 40,41 .…”

“…The condensation of aldehydes with two equivalents of 3-methyl-1-phenyl-5-pyrazolone is a conventional chemical approach to 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols). Many catalysts have been used for this transformation such as xanthan sulfuric acid 4 , phosphomolybdic acid 5 , silica sulfuric acid 6 , 3-aminopropylated silica gel 7 , sodium dodecyl sulfate 8 , [Cu(3,4-tmtppa)](MeSO 4 ) 4 9 , PEG-SO 3 H 10 , cellulose sulfuric acid 11 , lithium hydroxide monohydrate 12 , 1,3,5-tris(hydrogensulfato) benzene 13 , sulfuric acid ([3-(3-silicapropyl)sulfanyl]propyl)ester 14 , ethylenediammonium diacetate 15 , [Sipmim]HSO 4 16 , TEBA 17 , ceric ammonium nitrate 18 , silica-bonded S-sulfonic acid 19 , 2-hydroxyethylammonium acetate 20 , 1,3-disulfonic acid imidazolium tetrachloroaluminate 21 and 1-sulfopyridinium chloride 22 . Catalyst-free protocol and the electrocatalytic procedure were also applied to the preparation of 4,4'-(arylmethylene)bis(1H-pyrazol-5-ols) [23][24][25][26] .…”

Basic Magnetic Nanoparticles as Efficient Catalysts for the Preparation of Naphthopyrane Derivatives

“…The desired pure product(s) were characterised by comparison of their physical data with those of known compounds. [9][10][11][12][13][14][15][16][17][18][19][20][21][22] The spectral data of some representative naphthopyranes are as follows. …”

An efficient and green one-pot three-component synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol)s catalyzed by 2-hydroxy ethylammonium propionate

“…The condensation of aldehydes with two equivalents of 3-methyl-1-phenyl-5-pyrazolone is a known used route for synthesizing 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol)s. Xanthan sulfuric acid (4), phosphomolybdic acid (5), silica sulfuric acid (6), 3-aminopropylated silica gel (7), sodium dodecyl sulfate (8), tetramethyl-tetra-3,4-pyridinoporphyrazinato copper(II) methyl sulfate (9), poly(ethylene glycol)-bound sulfonic acid (10), cellulose sulfuric acid (11), lithium hydroxide monohydrate (12), 1,3,5-tris(hydrogensulfato) benzene (13), sulfuric acid ([3-(3-silicapropyl)sulfanyl]propyl)ester (14), ethylenediammonium diacetate (15), 2-hydroxy ethylammonium acetate (16), N-(3-silicapropyl)-N-methyl imidazolium hydrogen sulfate (17), benzyltriethylammonium chloride (18), ceric ammonium nitrate (19), silica-bonded S-sulfonic acid (20), 1,3-disulfonic acid imidazolium tetrachloroaluminate (21), and 1-sulfopyridinium chloride (22) can be used as catalysts for this transformation. Hasaninejad et al reported the synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol)s by the condensation of aldehydes with two equivalents of 3-methyl-1-phenyl-5-pyrazolone in the absence of catalyst (23)(24)(25).…”