Design and characterization of nano-silica-bonded 3-n-propyl-1-sulfonic acid imidazolium chloride {nano-SB-[PSIM]Cl} as a novel, heterogeneous and reusable catalyst for the condensation of arylaldehydes with β-naphthol and alkyl carbamates

Abstract

Design and characterization of nano-silica-bonded 3-npropyl-1-sulfonic acid imidazolium chloride {nano-SB- [PSIM]Cl} as a novel, heterogeneous and reusable catalyst for the condensation of arylaldehydes with b-naphthol and alkyl carbamates Abstract In this research, nano-silica-bonded 3-n-propyl-1-sulfonic acid imidazolium chloride {nano-SB-[PSIM]Cl} as a new and efficient Brønsted acidic ionic liquid supported on silica has been synthesized, and characterized using Fourier transform infrared spectroscopy, scanning electron microscopy, transmission electron microscopy, thermogravimetric, differential thermal gravimetric, X-ray diffraction, and energy-dispersive X-ray spectroscopy spectra. The presented silica-supported ionic liquid has been applied as a highly effective, heterogeneous, easy regenerable, and reusable catalytic system for the solvent-free condensation of arylaldehydes with b-naphthol and alkyl carbamates leading to a-carbamatoalkyl-b-naphthols. Once the nanocatalyst was regenerated and reused, no significant loss of its activity was observed.Graphical Abstract Design and characterization of nano-silica-bonded 3-n-propyl-1-sulfonic acid imidazolium chloride {nano-SB-[PSIM]Cl} as a novel, heterogeneous and reusable catalyst for the condensation of arylaldehydes with b-naphthol and alkyl carbamates. Electronic supplementary material The online version of this article (Keywords Nano-silica-bonded 3-n-propyl-1-sulfonic acid imidazolium chloride {nano-SB-[PSIM]Cl} Á Silica-supported Brønsted acidic ionic liquid Á Arylaldehyde Á b-Naphthol Á Alkyl carbamate Á a-Carbamatoalkyl-b-naphthol

Design, characterization, and use of N,N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et3N-SO3H]HSO4} as a novel and highly efficient catalyst for preparation of α,α′-bis(arylidene)cycloalkanones

“…Among several aspects of green chemistry, removal of volatile organic solvents from the reaction medium (i.e., use of solvent-free conditions) is of utmost importance. Furthermore, in many cases, solvent-free technique offers considerable synthetic advantages in terms of yield, selectivity, and simplicity of reaction procedure [16][17][18][19][20][21].…”

Synthesis of Naphthoxazinones in a One-Pot Two-Step Manner by the Application of Propylphosphonic Anhydride (T3P®)

“…1-Carbamatoalkyl 2-naphthols, important intermediates of biologically active compounds, can be easily prepared in a three-component reaction of 2-naphthol, methyl carbamate, and aromatic aldehydes (Scheme 1). Over the past decade, this condensation reaction has been investigated in the presence of various catalysts, such as cerium ammonium nitrate [4], ionic liquids [5][6][7][8][9][10][11][12], magnesium 2,2,2-trifluoroacetate [13], a non-ionic surfactant, Tween ® 20 [14], sulfamic acid-functionalized magnetic nanoparticles [15], tin tetrachloride [16], saccharin sulfonic acid [17], nanocrystalline TiO 2 -HClO 4 [18], magnesium hydrogen sulphate [19], silica perchloric acid [20], trityl chloride [21], silica-supported sodium hydrogen sulphate [22], and P 2 O 5 supported on SiO 2 [23]. The 1-carbamatoalkyl 2-naphthols can be converted further by hydrolysis or a ring closure.…”

Mesoporous Ionically Tagged Cross-Linked Poly(vinyl imidazole)s as Novel and Reusable Catalysts for the Preparation of N-Heterocycle Spiropyrans

“…Recently, we have reported a wide range of imidazolium- and pyridinium-based ILs and MSs functionalized with N -sulfonic acid tags for preparing heterocyclic compounds, energetic materials, and nitro compounds. − As a continuation of our previous investigation on the synthesis and applications of organic salts (ILs and MSs), herein, the synthesis of two novel nano-heterogeneous cross-linked and mesoporous ionically tagged polymers [PVI-SO 3 H]Cl ( 1 ) and [PVI-SO 3 H]­FeCl 4 ( 2 ) are reported (Scheme ). The synthesized polymers were fully characterized by Fourier transform infrared (FT-IR) spectroscopy, thermal gravimetry (TG), derivative thermal gravimetry (DTG), energy dispersive X-ray analysis (EDX), SEM-elemental mapping, scanning electron microscopy (SEM), transmission electron microscopy (TEM), nitrogen adsorption–desorption isotherm (Brunauer–Emmett–Teller, BET), and vibrating sample magnetometer (VSM).…”