30197-78-5

Usage

Uses

Used in Organic Synthesis:
2,3-dihydro-4H-chromen-4-ylidenepropanedinitrile is used as a building block for the synthesis of various organic compounds. Its unique structure allows for the creation of a wide range of chemical entities, making it a valuable asset in the field of organic chemistry.
Used in Medicinal Chemistry:
In the pharmaceutical industry, 2,3-dihydro-4H-chromen-4-ylidenepropanedinitrile is used as a key intermediate in the development of new drugs. Its structural properties enable the design and synthesis of novel therapeutic agents, potentially leading to advancements in medicinal treatments.
Used in Research and Development:
2,3-dihydro-4H-chromen-4-ylidenepropanedinitrile is employed as a research compound in academic and industrial laboratories. Its properties and reactivity are studied to gain insights into the behavior of similar compounds and to explore new synthetic pathways and applications.

Upstream product

• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 109-77-3 malononitrile 

Relevant academic research and scientific papers

Asymmetric organocatalytic vinylogous Michael addition triggered triple-cascade reactions of 2-hydroxycinnamaldehydes and vinylogous nucleophiles: construction of benzofused oxabicyclo[3.3.1]nonane scaffolds

An organocatalytic vinylogous Michael addition triggered triple-cascade reaction has been developed. 2-Hydroxycinnamaldehydes worked under iminium activation with either acyclic or cyclic ketone-derived α,α-dicyanoalkenes, yielding the benzofused oxabicyclo[3.3.1]nonanes bearing one quaternary stereocenter with excellent stereoselectivities.

Lipase-catalyzed highly diastereoselective direct vinylogous Michael addition reaction of α,α-dicyanoolefins to nitroalkenes

Lipase-catalyzed direct vinylogous Michael addition reactions of electron-deficient vinyl malononitriles to nitroalkenes are reported for the first time. A series of nitroalkenes reacting with vinyl malononitriles generate the corresponding products with

Enantioselective direct vinylogous Michael addition reaction catalyzed by organic molecules

Chiral 2-azanorbornyl-3-methanol is used as an organocatalyst for the highly enantioselective direct vinylogous Michael addition reaction of vinyl malononitriles to α,β-unsaturated aldehydes. In many cases, the products can be obtained in almost optically

Enantioselective Michael addition of dicyanoolefins to α,β- unsaturated aldehydes in aqueous medium

A pool of water-compatible catalysts, namely dialkyl-(S)-prolinols, has been developed for the enantioselective direct vinylogous Michael addition reaction of vinylmalononitriles to α,β-unsaturated aldehydes in aqueous medium. In many cases, the products can be obtained in almost optically pure form (>96% ee) after a single recrystallization.

Organocatalytic asymmetric allylic carbon-carbon bond formation

Organocatalytic allylic C-C bond-forming addition of activated alkylidenes to alkyl and aryl nitroalkenes has been achieved with high diastereo- and enantioselectivity. Chiral tertiary amine catalysts are used to give allyl intermediates which exhibit γ-s

Transfer hydrogenation of activated C=C bonds catalyzed by ruthenium amido complexes: Reaction scope, limitation, and enantioselectivity

(Chemical Equation Presented) It was found that the chemoselectivity could be completely switched from C=O to C=C bonds in the transfer hydrogenation of activated α,β-unsaturated ketones catalyzed by diamine-ruthenium complex. Moreover, this addition via metal hydride had been applied to the reduction of various activated olefins. The electron-withdrawing ability of functional groups substituted on C=C bonds at the α- or β-position had strong influence on the reactivity. In addition, a wide variety of chiral diamine-Ru(II)-(arene) systems was investigated to explore the asymmetric transfer hydrogenation of prochiral α,α-dicyanoolefins. Two parameters had been systematically studied, (i) the structure of the N-sulfonylated chiral diamine ligands, in which several chiral diamines substituted on the benzene ring of DPEN were first reported, and (ii) the structure of the metal precursors, and high enantioselectivitiy (up to 89% ee) at the β-carbon was obtained.

Synthesis of novel tricyclic heterocyclic compounds as potential anticancer agents using chromanone and thiochromanone as synthons

The arylmethylene of benzopyrane or benzothiopyrane 3,4 have been synthesized and condensed with hydrazine, guanidine and thiourea to yield pyrazole 5-8, aminopyrimidine 9,10 and thioxopyrimidine derivatives 11,12, respectively. Compounds 3 or 4 on treatment with malononitrile in the presence of ammonium acetate/acetic acid or in the presence of piperidine/ methanol to yield benzopyrano- and benzothiopyranopyridine 13,14 and benzopyrano- and benzothiopyrane 15,16, respectively. The oxirane of compound 3 is prepared and condensed with CS2 to yield the tricyclic system, thioxothienobenzopyrane 21. Ylidenemalononitrile for the ketone 1 and 2 are synthesized and condensed with aromatic aldehyde in presence of ammonium acetate/acetic acid to yield benzopyranopyridine and benzothiopyranopyridine derivatives 24,25, respectively, which are the isomer of compounds 13,14. Ylidenemalononitrile on condensation with phenylisothiocyanate yields benzo-pyrano- and benzothiopyranothioxopyridine 28,29, respectively.

SYNTHESE DE NOUVEAUX DERIVES 3-AMINO THIENO ET SELENOLOPYRIDINIQUES

Cyclisation of alkylidenemalonitriles by the Vilsmeier-Haack reagent gives 2-chloro 3-cyano pyridines.These compounds are used as starting material for the synthesis of thieno and selenolopyridines.Key words: Alkylidenemalonitriles; Vilsmeier-Haack; 2-chloro 3-cyano pyridines; thienopyridines; selenolopyridines.