33018-48-3

Upstream product

• 6783-05-7 trans-2-phenylvinylboronic acid 
• 708-06-5 2-hydroxynaphthalene-1-carbaldehyde 
• 37973-54-9 1,1-diacetoxy-3-phenylprop-2-ene 
• 135-19-3 β-naphthol 
• 14371-10-9 (E)-3-phenylpropenal 
• 536-74-3 phenylacetylene 
• 109-73-9 N-butylamine 
• 773-90-0 1-diazo-2(1H)naphthalenone 

Relevant academic research and scientific papers

Facile synthesis of 2h-benzo[h]chromenes via an arylamine-catalyzed mannich cyclization cascade reaction

A simple arylamine-catalyzed Mannich-cyclization cascade reaction was developed for facile synthesis of substituted 2H-benzo[h]chromenes. The notable feature of the process included the efficient generation of ortho-quinone methides (o-QMs) catalyzed by a

Pd-Catalyzed Formal [3 + 3] Heteroannulation of Allylic gem-Diacetates: Synthesis of Chromene-Based Natural Products and Exploration of Photochromic Properties

Palladium-catalyzed allylic alkylation reactions of allylic gem-diacetates are rarely explored. This work unveils an unusual chemical reactivity pattern of allylic gem-diacetates and establishes them as new prototypes to synthesize complex benzo[f]chromene systems. Under the reaction conditions, the diacetates behave as 1,3-dicationic equivalents and undergo a [3 + 3] heteroannulation with 2-naphthols (and meta-substituted phenols) to produce novel polycyclic chromenes possessing spiro-, tri-, and tetrasubstituted carbon centers. The versatility of the method is demonstrated in the synthesis of several chromene-based bioactive natural products. Further, interesting photochromic properties of the new classes of benzo[f]chromenes are also discovered.

Efficient synthesis of indene derivatives by cascade reactions

The present invention relates to an efficient synthesis method of indene derivatives through cascade reaction. In the present invention, a novel one-pot cascade approach to the synthesis of 1H-indene-3-carboxamides and 1H-indene-3-carboxylate derivatives through thermolysis of a diazo compound is developed. Along with various aromatic and heteroaromatic aldehydes, aliphatic or aromatic primary amine and aliphatic alcohol or phenol derivative are used as nucleophilic components. In the present invention, a multicomponent reaction without using a catalyst enables the synthesis of variously functionalized indene derivatives, and can be widely applied to the synthesis of natural products and medicine.

Intramolecular etherification and polyene cyclization of π-Activated Alcohols Promoted by Hot Water

Hot water, acting as a mildly acidic catalyst, efficiently promoted intramolecular direct nucleophilic substitution reactions of unsaturated alcohols with heteroatom or carbon nucleophiles. In a mixed solvent of water and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP), polyene cyclizations using allylic alcohols as initiators gave the desired cyclized products, and in neat HFIP, a tricyclization reaction gave a tetracyclic product in 51% chemical yield.

Lewis and Bronsted acid cocatalyzed reductive deoxyallenylation of propargylic alcohols with 2-nitrobenzenesulfonylhydrazide

Reductive deoxyallenylation of sterically hindered tertiary propargylic alcohols was realized on reaction with 2-nitrobenzenesulfonylhydrazide (NBSH) by the combined use of Lewis and Bronsted acid catalysts. This method features a broad substrate scope, m

Metalloradical approach to 2H -chromenes

Cobalt(III)-carbene radicals, generated through metalloradical activation of salicyl N-tosylhydrazones by cobalt(II) complexes of porphyrins, readily undergo radical addition to terminal alkynes to produce salicyl-vinyl radical intermediates. Subsequent hydrogen atom transfer (HAT) from the hydroxy group of the salicyl moiety to the vinyl radical leads to the formation of 2H-chromenes. The Co(II)-catalyzed process can tolerate various substitution patterns and produces the corresponding 2H-chromene products in good isolated yields. EPR spectroscopy and radical-trapping experiments with TEMPO are in agreement with the proposed radical mechanism. DFT calculations reveal the formation of the salicyl-vinyl radical intermediate by a metalloradical-mediated process. Unexpectedly, subsequent HAT from the hydroxy moiety to the vinyl radical leads to formation of an o-quinone methide intermediate, which dissociates spontaneously from the cobalt center and easily undergoes an endocyclic, sigmatropic ring-closing reaction to form the final 2H-chromene product.

Synthesis of diverse indene derivatives from 1-diazonaphthalen-2(1 H)-ones via thermal cascade reactions

A sequential Wolff rearrangement of 1-diazonaphthalen-2(1H)-ones followed by trapping of the ketene intermediate with primary and aromatic amines or alcohols and phenols in the presence of various aldehydes generates 1H-indene-3-carboxamides or 1H-indene-3-carboxylates. This constitutes an unprecedented three-component coupling reaction that allows for the synthesis of functionalized indene derivatives under catalyst-free thermal conditions.

Synthesis of 2H-chromenes in ionic liquid solvents

Vinylboronic acids react with o-hydroxyaryl aldehydes in room temperature ionic liquids in the presence of secondary amines to generate 2H-chromenes.