Efficient and General Synthesis of 3-Aryl Coumarins Using Cyanuric Chloride¹

Abstract

An efficient and general protocol for a rapid synthesis of different substituted 3-aryl coumarins is reported. A series of different substituted phenyl acetic acids have been successfully reacted with different substituted 2-hydroxy benzaldehydes in the presence of cyanuric chloride (2,4,6-trichloro-1,3,5-triazine) and N-methyl morpholine to afford 3-aryl coumarins in good to excellent yields.

Synthesis and biological evaluation of thiophosphate tricyclic coumarin derivatives as steroid sulfatase inhibitors

“…Many convenient synthetic methods have been described, including Pechmann [7], Perkin [8], Knoevenagel condensation [9], Reformatsky [10], and Wittig reactions [11]. Recent reports of the synthesis of coumarin derivatives include the use of metal triflates in qFriedel-Crafts alkenylations of aromatic compounds with various alkyl-and aryl-substituted alkynes [12], hydroarylation of arylpropionic acid methyl esters having a methoxymethyl acetal (MOM) protected hydroxy group with various arylboronic acids in the presence of a catalytic amount of CuOAc [13], reaction of substituted phenyl acetic acids and substituted 2-hydroxy benzaldehydes in the presence of cyanuric chloride (2,4,6-trichloro-1,3, 5-triazine) and N-methyl morpholine [14], palladium-catalyzed oxidative cyclocarbonylation of 2-vinylphenols [15], condensation of aroylketene dithioacetals, and 2-hydroxybenzaldehydes in the presence of a catalytic amount of piperidine [16], or reaction of 2-hydroxybenzaldehydes, triphenylphosphine, and dialkyl acetylenedicarboxylate via vinyltriphenylphosphonium salt-mediated aromatic electrophilic substitution [17].…”

Discovery of coumarin–monastrol hybrid as potential antibreast tumor-specific agent

“…The detailed reaction conditions for the synthesis of coumarin-monastrol hybrids are different substituted phenyl acetic acids in the presence of cyanuric chloride and N-methyl morpholine (NMM) in DMF for 1 h afforded the respective 3-aryl coumarin aldehydes [13] (3a-d) in excellent yield. Finally, the target compounds were synthesized via the Biginelli M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT 4 reaction involving 3-aryl coumarin aldehydes, ethyl aceto acetate and thiourea/urea in ethanol in the presence of catalytic amount of pTSA to afford coumarin-monastrol hybrid compounds (4)(5)(6)(7)(8)(9)(10).…”

A facile and practical p-Toluenesulfonic acid catalyzed route to dicoumarols containing an Aroyl group

“…2 The chemistry of coumarin derivatives has recently gained much attention from chemists owing to some interesting biological properties. [3][4][5] Dicoumarol was firstly discovered in moldy wet sweet-clover hay subsequent to which several methods have been reported for the development of its chemistry and synthesis of derivatives. Traditionally, the most popular strategies towards the synthesis of dicoumarols start from salicylaldehyde and formaldehyde 6 and involve the biosynthesis of dicoumarol using micro-organisms such as Penicillium jenseni, 7 or require the Knoevenagel condensation of 4-hydroxycoumarins with carbonyl compounds using several catalysts.…”