Sulfanilic acid: a versatile and efficient catalyst among various organoacids screened for the synthesis of 1-amidoalkyl-2-naphthols under solvent-free condition

Singh, Rajesh; Singh, Bhag; Duvedi, Robita; Kumar, Sahil

doi:10.1007/s11164-013-1513-5

Cited by 18 publications

(8 citation statements)

References 35 publications

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“…Sulfanilic acid is commercially available, economical, non polluting and easy to handle, non-inflammable, and a stable catalyst related to other organoacid catalysts which are eroding, costly and afford intensely acidic conditions. [40] Here we reported the use of sulfanilic as organocatalyst in one-pot three-component Mannich reaction for the synthesis of β-amino ketone.…”

Section: Figure 1: Medicinal Properties Of β-Amino Ketonementioning

confidence: 99%

Sulfanilic acid catalysed one‐pot three‐component Mannich reaction for synthesis of β‐amino ketones

Kulkarni¹

2020

Vietnam Journal of Chemistry

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We have reported sulfanilic acid as an exceedingly competent catalyst for one‐pot Mannich reaction to give β‐amino carbonyl compounds in good to excellent yield within a short reaction time. The various organic acids have screened; like gallic acid, 4‐hydroxy benzoic acid, 4‐amino benzoic acid, phenylacetic acid, chloroacetic acid, sulfosalicylic acid, sulfanilic acid, chloro benzoic acid, phthalic acid, salicylic acid, cinnamic acid, hippuric acid, 1‐naphthyl acetic acid, o‐amino benzoic acid, p‐TSA, succinic acid, malic acid, and among them sulfanilic acid is a suitable catalyst. The reaction condition was optimized with respect to the solvent, the amount of catalyst as well as the variation of the ketone, aldehyde, and amine substrates. The procedure is mild, effective, ecofriendly, and the use of the minimum amount of catalyst.

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Section: Figure 1: Medicinal Properties Of β-Amino Ketonementioning

confidence: 99%

Sulfanilic acid catalysed one‐pot three‐component Mannich reaction for synthesis of β‐amino ketones

Kulkarni¹

2020

Vietnam Journal of Chemistry

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“…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.…”

Section: Reviewmentioning

confidence: 99%

Mannich base-connected syntheses mediated by ortho-quinone methides

Barta¹,

Fülöp²,

Szatmári³

2018

Beilstein J. Org. Chem.

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This article provides an overview about specifically modified Mannich reactions where the process involves an ortho-quinone methide (o-QM) intermediate. The reactions are classified on the basis of the o-QM source followed by the reactant, e.g., the dienophile partner in cycloaddition reactions (C=C or C=N dienophiles) or by the formation of multicomponent Mannich adducts. Due to the important pharmacological activities of these reactive o-QM intermediates, special attention is paid to the biological activity of these compounds.

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“…Mechanistic rationale of Amidoalkyl-2-naphthols. or acetamides or acetonitrile in the presence of inorganic catalyst Ce(SO 4 ) 2 , [12] CeCl 3 ⋅ 7H 2 O, [25] Fe(HSO 4 ) 3 , HClO 4 -SiO 2 , [26] Al 2 O 3 -SO 3 H, [27] N-Bromo succinamide, [28] silica-supported molybdatophosphoric acid, [29] ytterbium triflate Yb(OTf) 3 , [30] and some organic catalyst triethyl benzyl ammonium chloride, [31] TMSCl/ NaI, [32] thiamine hydrochloride, [33] tetrachlorosilane, [34] succinic acid [35] and triflic acid, [36] deep eutectic solvent ([Choli-neCl][ZnCl2]3), [37] tannic acid, [38] zinc oxide nano particles, [39] and sulfanilic acid, [40] etc.…”

Section: Introductionmentioning

confidence: 99%

2,6‐Pyridinedicarboxylic Acid (PDCA) Catalyzed Improved Synthetic Approach for 1‐Amidoalkyl Naphthols, Dihydropyrimidin‐2(1H)‐ones and Bis‐indoles

Govindhan¹,

Nagarajan²

2021

ChemistrySelect

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An efficient and simple method for the synthesis of various amidoalkyl-2-naphthols, dihydropyrimidin-2(1H)-ones (DHPM) and bis-indoles has been developed using 2,6-pyridine dicarboxylic acid (PDCA), as an organocatalyst. All the reactions were performed through a one-pot multicomponent strategy. Reactants of the corresponding reaction were mixed in a single pot along with PDCA catalyst and suitable temperature and duration, yielded the corresponding products in moderate to excellent yield. The proposed method offers various advantages like shorter reaction time, operational simplicity, metalfree, readily accessible catalyst, no column chromatographic method, a cost-effective and acceptance of a wide range of substrates and good yields.

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Sulfanilic acid: a versatile and efficient catalyst among various organoacids screened for the synthesis of 1-amidoalkyl-2-naphthols under solvent-free condition

Cited by 18 publications

References 35 publications

Sulfanilic acid catalysed one‐pot three‐component Mannich reaction for synthesis of β‐amino ketones

Sulfanilic acid catalysed one‐pot three‐component Mannich reaction for synthesis of β‐amino ketones

Mannich base-connected syntheses mediated by ortho-quinone methides

2,6‐Pyridinedicarboxylic Acid (PDCA) Catalyzed Improved Synthetic Approach for 1‐Amidoalkyl Naphthols, Dihydropyrimidin‐2(1H)‐ones and Bis‐indoles

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