n-Dodecylbenzene Sulfonic Acid (DBSA) as a Novel Brønsted Acid Catalyst for the Synthesis of Bis(indolyl)methanes and Bis(4-hydroxycoumarin-3-yl)methanes in Water

Abstract

n-Dodecylbenzene sulfonic acid (DBSA) as a novel, biodegradable, and efficient Brønsted acid catalyst used for the reaction of indoles/4-hydroxy coumarin with aldehydes to obtain a bis(indolyl)methanes/bis(4-hydroxycoumarin-3yl)methanes, respectively. The catalyst exhibited remarkable activity, and tolerated a wide variety of functional groups providing the desired bis(indolyl)methanes and bis(4-hydroxycoumarin-3-yl)methanes in good to excellent yield (70% -96%) in water.

Fe3O4@SiO2@Im‐bisethylFc [HC2O4] as a novel recyclable heterogeneous nanocatalyst for synthesis of bis‐coumarin derivatives

“…These derivatives have been found useful in an extensive range of biological and pharmaceutical actions, including enzyme inhibitors, anticoagulants, antioxidants, antitumor drugs, anti‐diabetic (α‐glucosidase inhibitors) urease inhibitors, anticancers, antibacterials, inhibit c‐Met phosphorylation in BaF 3 /TPR‐Met and EBC‐1 NSCLC cell lines, antimicrobial, antiviral, proliferation inhibition of K‐562 and inhibit HIV‐1 . Recently, several methods have been reported for the synthesis of bis‐coumarin by the reaction of 4‐hydroxycoumarin and various aldehydes in the presence of various homogeneous and heterogeneous catalysts and under various reaction conditions, such as tetrabutylammonium bromide (TBAB), molecular iodine, [bmin] BF 4 , SO 3 H‐functionalized IL, sodium dodecyl sulfate, piperidine, n‐dodecylbenzene sulfonic acid (DBSA), [pyridin‐SO 3 H]Cl, TrBr and [Fe 3 O 4 @SiO 2 @(CH 2 ) 3 ‐Im‐SO 3 H]Cl, MNPs‐PSA and Fe 3 O 4 @SiO 2 @(CH 2 ) 3 semicarbazide‐SO 3 H/HCl . Although all the procedures for the synthesis of corresponding bis‐coumarin have their merits, the main disadvantages of these methods are often tedious work‐up procedures, low yields, harsh reaction conditions, and the use of toxic, corrosive and expensive catalysts, and the recovery of these catalysts are often difficult.…”

Synthesis of biscoumarin derivatives as biological compounds using cellulose sulfonic acid

“…In view of different biological and chemical applications of biscoumarin, the development of suitable synthetic methodologies for their generation has been a topic of great interest in recent times. The general method for synthesis of biscoumarin derivatives involves the reaction of 4hydroxycoumarin with aryl aldehydes in the presence of different catalysts such as tetrabutylammonium bromide [12], molecular iodine [13], [bmin] BF4 [14], SO3H-functionalized ionic liquid [15], sodium dodecyl sulfate [16], piperidine [17], n-dodecylbenzene sulfonic acid (DBSA) [18], nano silica chloride [19], ruthenium (III) chloride hydrate [20] and Zn (proline)2 [21]. Although these methods may be effective, some of them have relatively long reaction times and tedious work up.…”

Cobalt(II) Chloride Hexahydrate as an Efficient and Inexpensive Catalyst for the Preparation of Biscoumarin Derivatives

“…A number of methods have been reported for the synthesis of these compounds in the presence of various catalysts like molecular iodine [7], sodium dodecyl sulfate (SDS) [8], tetrabutylammonium bromide (TBAB) [9], ( [11], sulfated titania (TiO 2 /SO 4 2− ) [12], ruthenium(III) chloride hydrate (RuCl 3 ⋅nH 2 O) [13], n-dodecylbenzene sulfonic acid (DBSA) [14], and silica chloride nanoparticles (nano SiO 2 Cl) [15]. However, these methods suffer from one or more disadvantages such as low yields of products, long reaction times, use of expensive catalyst, toxic solvents, or harsh reaction conditions.…”