A convenient three-component synthesis of carbamatoalkyl naphthols catalyzed by cerium ammonium nitrate

Abstract

ABSTRACT.A highly efficient synthesis of carbamatoalkyl naphthols has been performed by a one-pot threecomponent condensation of 2-naphthol, aldehydes, and methyl/ethyl/benzyl carbamates in the presence of cerium ammonium nitrate under solvent-free conditions at 70 o C. The solvent, optimal amounts of raw materials and catalyst, and reaction temperature are investigated. Experimental results show that only 0.1 mmol catalyst is enough to induce the conversion. Most reactions are performed within a short reaction time. The structures of all products were characterized by IR, 1 H NMR, 13 C NMR, MS, and elemental analysis. A mechanism to rationalize the reaction has been proposed.

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.…”

Succinimide-N-sulfonic acid as an efficient recyclable catalyst for the synthesis of some fused indolo pyrano pyrimidinone derivatives

“…We have also reported the application of TUD for the synthesis of 3,4-dihydropyrano[c]chromenes and 6-amino-5-cyano-4-aryl-2-methyl-4H-pyrans in water [26]. Multicomponent reactions (MCRs) allow the creation of several bonds in a single operation and are attracting increasing attention as one of the most powerful emerging synthetic tools for the creation of molecular diversity and complexity [32][33][34].…”