Three-Component reaction between 2-naphthol, Aromatic Aldehydes and Acetonitrile in the Presence of Chlorosulfonic Acid Yields 1-(Acetylamino (Aryl)Methyl)-2-Naphthols

Abstract

The one-pot, three-component reaction between aryl aldehydes, 2-naphthol, and acetonitrile in the presence of chlorosulfonic acid affords 1-[acetylamino(aryl)methyl]-2-naphthols in excellent yields.

A Three-Component Novel Synthesis of 1-[Aryl(Thioacetamido)Methyl]-2-Naphthol Derivatives

“…These signals are related to OH and NH protons. 13 C NMR spectrum of compound 4a showed 17 distinct signals in agreement with the proposed structure.…”

“…13 The reaction proceeds through the in situ formation of o-quinone methides (o-QMs), and acetonitrile acted as a nucleophile. We describe here a practical and inexpensive method for the preparation of new 1-[aryl(thioacetamido)meth yl]-2-naphthol derivatives via a three-component condensation reaction between aryl aldehydes 3, 2-naphthol 1, and thioacetamide 2 in the presence of 0.1 mmol of p-toluenesulfonic acid (p-TSA) in refluxing 1,2-dichloroethane after 1h afforded 1-[aryl(thioacetamido)methyl]-2-naphthols (Scheme 1).…”

Citric Acid Catalyzed Synthesis of Amidoalkyl Naphthols under Solvent-free Condition: An Eco-friendly Protocol

“…Synthesis of amidoalkyl naphthols can be carried out by the multi-component condensation of aldehydes, 2-naphthols and amide/urea in the presence of Lewis or Bronsted acid catalysts such as chlorosulphonic acid [11], p-toluene sulphonic acid [12], NaHSO 4 .H 2 O [13], Fe(HSO 4 ) 3 [14], Sr(OTf) 2 [15], Iodine [16], hetropoly acid K5CoW12O40.3H 2 O [17], and hetropoly acid catalysts like cation-exchange resins [18], silica supported perchloric acid [19,20], FeCl 3 .SiO 2 [21], montmorillonite K10 clay [22], silica sulfuric acid [23], sulfamic acid [24,25], N,N,N',N'-tetrabromobenzene-1,3-disulfonamide [26]. Moreover, very recently P 2 O 5 /SiO 2 [27] magnetic nanoparticle-supported sulfuric acid [28] and MCM-41-N-propylsulfamic acid [29] has been used to carry out the synthesis.…”

“…Moreover, very recently P 2 O 5 /SiO 2 [27] magnetic nanoparticle-supported sulfuric acid [28] and MCM-41-N-propylsulfamic acid [29] has been used to carry out the synthesis. However some of the above reported methods suffer from disadvantages such as long reaction times [17], the use of expensive reagents [15], low yields of products [24,25], high catalyst loading [23], corrosive reagents [11], strongly acidic conditions [19,20] and the use of an additional microwave oven [14], or ultrasonic irradiation [23]. Therefore, to overcome these limitations, the discovery of a new, eco-friendly and easily available catalyst with high catalytic activity and short reaction time for the preparation of amidoalkyl naphthols is still desirable.…”

Syntheses and transformations of carbamatoalkylnaphthols prepared via modified Mannich reactions

“…23 SiO 2 -supported Preyssler nanoparticles were found to be an effective catalyst for the preparation of acetamidonaphthols 2a-c,e-g,j,m (86-92%) in a short reaction time (3-8 min proved to be efficient enough to extend the series of aldehydes to aliphatic aldehydes and naphthaldehydes, leading to 2w,y in moderate yields (42-74%). 14 The process was later optimized for 2a-c,g,h,j,m,o,q,u,w,y, when, instead of heating of the reaction in MeCN, a mixture of acetyl chloride and 4 mol% I 2 was applied as catalyst (Scheme 1).…”