Zinc Benzenesulfonate–Promoted Eco-Friendly and Efficient Synthesis of 1-Amidoalkyl-2-naphthols

Abstract

A three-component, one-pot condensation of 2-naphthol, aldehydes, and amides catalyzed by zinc benzenesulfonate gives 1-amidoalkyl-2-naphthols in good yields at 80 C under solvent-free conditions. The catalytic activities of zinc benzenesulfoante and 12 other metal benzenesulfonates were compared. After the reaction, zinc benzenesulfoante can be recycled several times without distinct loss of catalytic activity.

Reaction between thiocarbamidoalkyl naphthols and acetylenic esters: An interesting cyclocondensation reaction for the synthesis of new thiazolidin-4-one derivatives

“…It is, therefore, not surprising that a considerable number of protocols for the synthesis of these compounds by three-component condensation of aldehydes, β-naphthol and acetonitrile or amides/carbamates or urea in the presence of different catalysts have been reported. [2][3][4][5] However, in consequence of the lower reactivity of the thio analogues of amide and urea, only limited published information regarding the replacement of amide with thioamide or thiourea are available in the literature. [6][7][8][9] The thioamido-and thiocarbamidoalkyl naphthols which were produced by these methods can be used as convenient building blocks in the synthesis of sulfur and nitrogen containing heterocyclic compounds.…”

Solvent free synthesis of amidoalkyl derivatives under green and convenient conditions

“…Amido alkyl derivatives have been synthesis with different homogeneous and heterogeneous catalysts like acidic catalysts [5,11–30], magnetic catalysts [31–33], ionic liquid [34–36], and metallic nanoparticles [37–41]. Some of them have disadvantages like long reaction times, low product yields, using of hazardous solvents, synthesis of catalysts in several stages, and use of expensive materials to the synthesis of catalysts.…”

β‐Cyclodextrin‐Monosulphonic Acid Catalyzed Efficient Synthesis of 1‐Amidoalkyl‐2‐naphthols

“…They can be synthesized from the condensation reaction between 2‐naphthol, aromatic aldehydes and amides. The catalysts reported so far for the synthesis of these biologically important compounds are p‐TSA, K 5 CoW 12 O 40 .3H 2 O, montmorillonite K10, Fe(HSO 4 ) 3 , silica gel supported Ionic liquid, Zwitterionic‐type molten salt, sulfonic acid functionalized imidazolium salts, MoO 3 ‐ZrO 2 , silica chloride, [Dsim]HSO 4 , cellulose‐SO 3 H, MCM‐41‐N‐propylsulfamic acid, MNPs‐SO 3 H, MNPs‐IL‐OAc, MNPs‐PhSO 3 H, MSNs‐HPZ‐SO 3 H, Fe 3 O 4 ‐CNTs, H 4 SiW 12 O 40 /TPI‐MCM‐41, H 3 N + SO 3 − , I 2 , molybdophosphoric acid, HClO 4 ‐SiO 2 , P 2 O 5 , H 3 PW 12 O 40 , BAILs, [NMP][HSO 4 ], ZBS, SILC, boric acid, HPA/TPI‐Fe 3 O 4 , nano‐S 8 , β‐CD‐BSA, {[C 6 (MPy) 2 ][CoCl 4 ] 2− }, LSA, graphene oxide, barium phosphate nano‐powder, AgNPs, Co (II) Schiff base complex, Zinconocene dichloride and SO 3 H‐MCM‐41@NiFe 2 O 4 …”