42189-35-5

Upstream product

• 135-02-4 ortho-anisaldehyde 
• 90-02-8 salicylaldehyde 
• 50978-45-5 3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide 
• 86-52-2 1-Chloromethylnaphthalene 
• 13922-41-3 1-Naphthylboronic acid 
• 91-64-5 coumarin 
• 201230-82-2 carbon monoxide 
• 1407546-33-1 2-chloro-2-(naphthalen-1-yl)acetaldehyde 
• 1407546-37-5 2-chloro-2-(naphthalen-1-yl)ethan-1-ol 
• 62222-40-6 2-(1-naphthyl)oxirane 
• 66-77-3 1-naphthaldehyde 
• 132-75-2 naphthalen-1-ylacetonitrile 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 68-12-2 N,N-dimethyl-formamide 

Relevant academic research and scientific papers

A Photochemical Synthesis of 3-Arylcoumarins

A number of fluorescent 3-arylcoumarins (3-aryl-2H-1-benzopyran-2-ones) have been synthesized by the photo-coupling of 3-bromocoumarin with aromatic and heteroaromatic compounds.The structure of 3-(1-naphthyl)coumarin was confirmed by X-ray crystallography.

Facile one-pot synthetic access to libraries of diversely substituted 3-aryl (Alkyl)-coumarins using ionic liquid (IL) or conventional base/solvent, and an IL-mediated approach to novel coumarin-bearing diaryl-ethynes

The in-situ formed carbonylimidazole derivatives of Ar(alkyl)-CH2COOH react at r.t. with substituted salicylaldehydes in [BMIM][PF6] or [BMIM][BF4] as solvent, and [PAIM][NTf2] as basic-IL, to produce libraries of 3-aryl(alkyl)coumarins. Whereas these reactions can also be performed with similar efficiency in THF by employing DBU, the IL approach offers easier work-up and recycling of the IL solvent. An IL-mediated approach to the synthesis of novel coumarin-bearing diaryl-ethynes by the Sonogshira reaction is also reported, and the potential for recycling/reuse of the IL solvent is shown.

Pd-catalysed carbonylative annulation of salicylaldehydes with benzyl chlorides using N-formylsaccharin as a CO surrogate

A convenient and highly efficient Pd-catalysed carbonylative annulation of salicylaldehydes with benzyl chlorides to afford the corresponding 3-arylcoumarins in good to excellent yields has been developed. Importantly, the protocol utilizes a commercially available, low cost, solid and easy to handle N-formylsaccharin as an alternative to the highly toxic CO gas.

Ultrasound-Assisted Solvent-Free Parallel Synthesis of 3-Arylcoumarins Using N-Acylbenzotriazoles

An ultrasound-assisted one-pot acylation/cyclization reaction between N-acylbenzotriazoles and 2-hydroxybenzaldehydes has been developed for the synthesis of substituted 3-arylcoumarins. Using ultrasound not only allows rapid and clean conversion but also simplifies experimental setup and parallel workup leading to rapid generation of 3-arylcoumarin libraries under mild, solvent-free, and chromatography-free conditions.

KMnO4/AcOH-mediated C3-selective direct arylation of coumarins with arylboronic acids

An efficient protocol for KMnO4/AcOH-mediated dehydrogenative direct radical arylation of coumarins with arylboronic acids to afford 3-arylcoumarin derivatives is described. A similar reaction system is also applicable to the 3-arylation of quinolinone derivatives. These KMnO4/AcOH-mediated coupling reactions occur regioselectively at the C3 position of coumarins and quinolinones. Some notable features of this method are high efficiency, moderate to good yield, and a broad group tolerance.

A general palladium-catalyzed carbonylative synthesis of chromenones from salicylic aldehydes and benzyl chlorides

Cute CO! An interesting and straightforward procedure for the carbonylative synthesis of chromenones from readily available salicylic aldehydes and benzyl chlorides has been developed (see scheme; DPPP=1,3-bis(diphenylphosphino) propane). In the presence of a palladium catalyst, various coumarins were produced in good to excellent yields. Copyright

Synthesis of 3-arylcoumarins through N-heterocyclic carbene catalyzed condensation and annulation of 2-chloro-2-arylacetaldehydes with salicylaldehydes

The condensation reaction of 2-chloro-2-arylacetaldehyde with salicylaldehyde catalyzed by N-heterocyclic carbene (NHC) leading to 3-arylcoumarin was studied. A number of 3-arylcoumarin derivatives were obtained in good to excellent yields via this umpolung reaction. This reaction is facile and experimentally simple and mild.

Three-component coupling using arynes and DMF: Straightforward access to coumarins via ortho-quinone methides

ortho-Quinone methides, arising from a formal [2+2] cycloaddition between arynes and DMF, were found to facilely undergo a [4+2] cycloaddition with ester enolates or ketenimine anions to produce diverse coumarins in a straightforward manner. The Royal Society of Chemistry 2011.

Single-compound libraries of organic materials: Parallel synthesis and screening of fluorescent dyes

"Hits" with high quantum yields: The screening of the chromophores of a coumarin library for optical properties allowed the identification of "hits" with high fluorescence quantum yields (see picture) which could be used as fluorescence labels and laser dyes. The generation of the library was facilitated by an efficient method involving the parallel synthesis utilizing Pd-catalyzed cross-coupling reactions.

Synthesis of new 3-(α-naphthyl)coumarins

The preformed complex of POCl3 and N,N-diethyl-(α-naphthyl)acetamide (2) reacts with substituted salicylaldehydes (3) to yield differently substituted, hitherto unknown 3-(α-naphthyl)coumarins (1).