107752-89-6

Basic information

• Product Name: 2-amino-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
• Synonyms: 2-amino-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
• CAS NO: 107752-89-6
• Molecular Formula: C₁₆H₁₄N₂O₂
• Molecular Weight: 266.3
• Mol File: 107752-89-6.mol
• Article Data: 75

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-amino-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile(107752-89-6)
• EPA Substance Registry System: 2-amino-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile(107752-89-6)

Safety Data

• Hazardous Substances Data: 107752-89-6(Hazardous Substances Data)

Usage

Properties

Chemical compound with a complex structure
Contains an amino group, a carbonyl group, a phenyl group, and a carbonitrile group
Arranged within a tetrahydrochromene ring system
Potential biological activities and pharmaceutical relevance
Used in medicinal chemistry for synthesis of novel drugs
Used in development of new materials and fine chemicals
Relevance in the study of organic chemistry and chemical reactivity

Specific Content

2-amino-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
Tetrahydrochromene ring system
Amino group
Carbonyl group
Phenyl group
Carbonitrile group
Unique structure and functional groups
Potential for diverse chemical reactions

Upstream product

• 504-02-9 1,3-cylohexanedione 
• 100-52-7 benzaldehyde 
• 109-77-3 malononitrile 
• 30182-67-3 1,3-Cyclohexanedione 
• 31771-33-2 2-phenyl-4,4,6-trimethyltetrahydro-(2H)-1,3-oxazine 
• 2700-22-3 Benzylidenemalononitrile 

Downstream Products

• 1610831-62-3 2-cyano-4-oxo-3-phenyl-2,3,4,5,6,7-hexahydrobenzofuran-2-carboxamide 
• 1272972-07-2 2,4-diamino-6,7,8,9-tetrahydro-6-oxo-5-phenyl-5H-chromeno[2,3-b]pyridine-3-carbonitrile 
• 1272972-01-6 C₂₂H₁₈N₂O₂S 
• 1272972-00-5 C₂₂H₁₈N₂O₃ 
• 1272972-08-3 4-amino-3-cyano-1H-10-phenyl-6,7,8,10-tetrahydro-9-oxa-1-azaanthracen-2,5-dione 
• 1272972-14-1 N-(3-cyano-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromen-2-yl)chloroacetamide 
• 1272971-96-6 C₁₉H₁₈N₂O₃ 

Relevant articles and documents

Introduction of taurine (2-aminoethanesulfonic acid) as a green bio-organic catalyst for the promotion of organic reactions under green conditions

Taurine (2-aminoethanesulfonic acid), a semi-essential amino acid that exists in the human body and numerous other living creatures, is used as a green bio-organic catalyst for the promotion of the Knoevenagel reaction between aldehydes and malononitrile. In the same way, tetraketones can also be produced through a Knoevenagel reaction, followed by Michael addition. 2-Amino-3-cyano-4H-pyran derivatives are simply prepared via a three-component reaction in the presence of taurine as the catalyst. All these reactions are performed in water, a green solvent. The advantages of using of taurine as the catalyst are it is environmentally friendly, low cost, commercially available, easy to separate from the reaction mixture, and has high reusability. Use of this catalyst results in acceptable reaction times, high yields and high purities of the obtained products without utilizing any organic solvents.

The implication of electrocatalysis in MCR strategy: Electrocatalytic multicomponent transformation of cyclic 1,3-diketones, aldehydes and malononitrile into substituted 5,6,7,8-tetrahydro-4H-chromenes

The electrochemically induced catalytic multicomponent transformation of cyclic 1,3-diketones, aldehydes and malononitrile in alcoholic solvents results in the formation of substituted 5,6,7,8-tetrahydro-4H-chromenes in 85-95% yields. The reaction is perf

Nanostructured coumarin-based cobalt complex as an efficient, heterogeneous and recyclable catalyst for the three-component synthesis of benzo[b]pyran and 3,4-dihydropyrano[c]chromene derivatives

Abstract: An improved one-pot three-component reaction of carbonyl compounds (dimedon, 4-hydroxy coumarin and 1,3-cyclohexadion) with malononitrile and aryl aldehydes in aqueous media (H2O:EtOH) as a solvent with short reaction time for the synthesis of benzo[b]pyran and 3,4- dihydropyrano[c]chromane derivatives by using nanostructured coumarin-based cobalt complex as an efficient heterogeneous catalyst. The salient features of this new protocol include simple procedure, high yields, easy isolation of products without need to column chromatography and short reaction times. Also, the nanocatalyst was recovered by adding EtOH and reused five times without significant loss of its catalytic activity. Biological impact assessments of the complex were conducted by DNA cleavage ability assay and eukaryotic cell toxicity measurement. Although the complex showed single-strand DNA breakage under oxidative conditions, its high polar nature revealed a marked decrease in cell toxicity data due to the restriction on cell entry. Graphic abstract: [Figure not available: see fulltext.]

Catalyst-free UV365-assisted synthesis of pyran annulated heterocyclic scaffolds and evaluation of their antibacterial activities

A convenient and eco-friendly, one-pot synthetic protocol for pharmaceutically important pyran-based heterocyclic compounds is repeated herein. The reactions were carried out at room temperature in a water–ethanol solvent mixture under direct irradiation

A cytochrome c-urea functionalized dipeptide conjugate: An efficient HBD framework to synthesize 4: H -pyrans via one-pot multicomponent reaction

This work is focused on the development of an efficient and green protocol for the one-pot multicomponent synthesis of a series of 4H-pyran derivatives. Herein, a protein-peptide conjugate (SS1-Cyt. c) is synthesized and characterized using Circular Dichr

Synthesis, Characterization, and Catalytic Behavior of Bamboo Rice Husk Ash

In this paper, we report the use of bamboo rice husk ash as an efficient, greener, reusable, and biodegradable heterogeneous catalyst for the synthesis of tetrahydro-4H-chromene-3-carbonitriles via the one-pot three-component reaction of malononitrile wit

Facile: In situ synthesis and characterization of a novel PANI/Fe3O4/Ag nanocomposite and investigation of catalytic applications

A novel magnetic polyaniline (PANI)/Fe3O4/Ag nanocomposite was successfully synthesized via in situ polymerization induced by ultraviolet irradiation (λ = 254 nm) in the presence of Fe3O4 nanoparticles and Ag cations as oxidants. The morphology and structure of the newly prepared nanocomposite was characterized by Fourier-transform infrared spectrometry, X-ray diffraction, energy-dispersive X-ray spectrometry, vibrating sample magnetometry, transmission electron microscopy, field-emission scanning electron microscopy and inductively coupled plasma optical emission spectrometry. The corresponding saturation magnetization for the nanocomposite was about 20.37 emu g-1. The catalytic properties of the nanocomposite were evaluated in the synthesis of biologically and pharmaceutically important pyran derivatives and it was shown to produce high yields, short reaction times and an easy work-up process. The superparamagnetic properties of the nanocatalyst allowed easy separation from the reaction media.

Synthesis and characterization of poly(4-vinylpyridine)/MCM-48 catalyst for one-pot synthesis of substituted 4H-chromenes

In this paper, we wish to report the synthesis and characterization of poly(4-vinylpyridine) supported on MCM-48 by in situ polymerization of 4-vinylpyridine in the presence of MCM-48. This catalyst was effectively employed as a novel heterogeneous basic

Basic ionic liquid-catalyzed multicomponent synthesis of tetrahydrobenzo[b]pyrans and pyrano[c]chromenes

Triethylenetetraammonium trifluoroacetate-catalyzed condensation of benzaldehydes, malononitrile and cyclic 1,3-dioxo compounds in aqueous medium affords the corresponding fused 2-amino-4-aryl-3-cyanopyrans.

Improvement in nanocomposite host (nanocavity of dealuminated zeolite Y)-guest (12-molybdophosphoric acid) catalytic activity and its application to the one-pot three-component synthesis of tetrahydrobenzo[b]pyrans

Zeolite Y was dealuminated by chemical methods (with ethylenediaminetetraacetic acid) to modify the zeolite structure for 12-molybdophosphoric acid (MPA) loading. MPA was encapsulated in the nanocavities of modified dealuminated zeolite Y (MDAZY) and char

One-pot synthesis of polyfunctionalized pyrans catalyzed by basic ionic liquid in aqueous media

(Chemical Equation Presented) An efficient and convenient method for the synthesis of polyfunctionalized 4H-pyrans has been achieved through the one-pot condensation of aromatic aldehydes, malononitrile, and 4-hydroxycoumarin, phenols or active methylene

Ultrasound promoted facile one pot synthesis of highly substituted pyran derivatives catalyzed by silica-coated magnetic NiFe2O4 nanoparticle-supported H14[NaP5W30O110] under mild condition

Silica-coated magnetic NiFe2O4 nanoparticle-supported Preyssler heteropolyacid (H14[NaP5W30O110]) catalyzed efficiently the synthesis of highly substituted pyran derivatives under ultrasoni

A highly active FeNi3-SiO2 magnetic nanoparticles catalyst for the preparation of 4H-benzo[b]pyrans and Spirooxindoles under mild conditions

A green and efficient method for the synthesis of various 4H-benzo[b]pyrans and Spirooxindoles in the presence of FeNi3-SiO2 as the nanocatalyst at room temperature is reported. High catalytic activity and ease of recovery from the r

Trichloroisocyanuric Acid as a Highly Efficient Catalyst for the Synthesis of Tetrahydrobenzo[b]pyran Derivatives

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Anion-cation co-operative catalysis by artificial sweetener saccharine-based ionic liquid for sustainable synthesis of 3,4-dihydropyrano[: C] chromenes, 4,5-dihydropyrano[4,3- b] pyran and tetrahydrobenzo [b] pyrans in aqueous medium

In this study, a saccharine-based ionic liquid [Bmim]Sac has been found to be a sustainable catalyst for the synthesis of 3,4-dihydropyrano[c]chromenes, 4,5-dihydropyrano[4,3-b]pyran and tetrahydrobenzo[b]pyrans scaffolds through Domino Knoevenagel-Michae

Efficient synthesis of 2-amino-3-cyano-4H-pyran derivatives via a non-catalytic one-pot three-component reaction

Abstract: A convenient one-pot multi-component strategy was conducted successfully under catalyst-free conditions employing water and PEG-400 as the efficient and cheap promoting medium. Three types and nearly 50 2-amino-3-cyano-4H-pyran annulated derivat

Novel magnetic nanoparticles Fe3O4-immobilized domino Knoevenagel condensation, Michael addition, and cyclization catalyst

The synthesis, characterization and applications of guanidine supported on magnetic nanoparticles Fe3O4 (MNPs-Guanidine) as a novel magnetically separable base nanocatalyst are described. We have studied the application of this new c

Fe3O4–SiO2–Bi2O3-catalyzed One-Pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives Under Solvent-Free Conditions

Abstract: A Fe3O4–SiO2–Bi2O3 magnetic nanocatalyst was used to synthesize tetrahydrobenzo[b]pyran derivatives from malononitrile, cyclohexane-1,3-dione, and benzaldehyde derivatives at 80°C under solv

Ferrocene-Functionalized Dithiocarbamate Zinc(II) Complexes as Efficient Bifunctional Catalysts for the One-Pot Synthesis of Chromene and Imidazopyrimidine Derivatives via Knoevenagel Condensation Reaction

Four new mononuclear/coordination polymeric (CP) zinc(II) complexes (1-4) of ferrocenyl/pyridyl-functionalized dithiocarbamate ligands, N-ferrocenylmethyl-N-butyl dithiocarbamate (L1), N-ferrocenylmethyl-N-ethylmorpholine dithiocarbamate (L2), N-ferroceny