Efficient and solvent-free synthesis of 1-amidoalkyl-2-naphthols using N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide

Abstract

Abstract:

Eco-friendly synthesis of amidochloroalkylnaphthols and its related oxazepinones with biological evaluation

“…Several reports have described the synthesis of amidoalkylnaphthols through multicomponent condensation of aryl aldehydes, 2-naphthol, and carboxylic acid amides in the presence of a Lewis or Bronsted acid catalysis, generally under thermal conditions [31][32][33][34][35][36][37][38][39][40]. Thus, multicomponent condensation of aldehydes, 2-naphthol, and nitriles to give amidoalkylnaphthols in a Ritter-type reaction was also reported [41][42][43][44][45][46][47][48][49].…”

Mannich base-connected syntheses mediated by ortho-quinone methides

“…In additional publications listed in Table 1, entries 42–64, phosphorus pentoxide (P 2 O 5 ) [46], silica-supported phosphorus pentoxide (P 2 O 5 -SiO 2 ) [47], N , N , N ’, N ’-tetrabromobenzene-1,3-disulfonamide (TBBDA) [48], 1-methyl-3-(2-(sulfoxy)ethyl)-1 H -imidazol-3-ium chloride (MSI) [49], succinic acid [50], tannic acid [49], p -nitrobenzoic acid [52], a carbon-based solid acid (CBSA) [53], citric acid [54], sulfanilic acid [55], bismuth(III) nitrate pentahydrate (Bi(NO 3 ) 3 ·5H 2 O) [56], 1-hexanesulfonic acid sodium salt [57], zirconyl triflate (ZrO(OTf) 2 ) [58], sulfonated carbon (SO 3 H-carbon) [59], MCM-41- N -propylsulfamic acid [60], polyphosphate ester [61] and amberlite IR-120 [62] were used as catalysts. These latest strategies provide efficient syntheses under mild conditions without using harsh chemicals.…”

Choline peroxydisulfate oxidizing Bio-TSIL: triple role player in the one-pot synthesis of Betti bases and gem-bisamides from aryl alcohols under solvent-free conditions

“…By attaching different functional groups on the cation, ionic liquids, able to perform a specific task can be obtained. However these protocols [37][38][39][40][41][42] have several drawbacks like, use of aldehyde, high toxicity, corrosion, catalyst waste, use of toxic organic solvents, rigorous condition, high reaction temperature, long reaction times, byproduct formation, difficulty in separation and recovery. Davis and co-workers introduced task-specific ionic liquids.…”

“…In the present study, as part of an our ongoing research on the development of green solvents in organic synthesis, 44,45 we proceeded to explore catalytic and oxidant activity of the recently reported environmental friendly biodegradable oxidizing TSIL ChPS 46 1 (Fig. 41 1 is a choline based oxidizing TSIL; while ChBS 2 reduced TSIL (Fig. 1 can be easily and inexpensively synthesized, starting from Choline chloride and potassium peroxydisulfate.…”