36937-71-0

Basic information

• Product Name: 2H-1-Benzopyran-3-carbonitrile, 2-imino-
• Synonyms: 2-iminocoumarin-3-carbonitrile;2-iminobenzopyran-3-carbonitrile;2-imino-2H-1-benzopyran-3-carbonitrile;2-Imino-2H-chromene-3-carbonitrile;2H-1-Benzopyran-3-carbonitrile,2-imino
• CAS NO: 36937-71-0
• Molecular Formula: C10H6N2O
• Molecular Weight: 170.17
• Mol File: 36937-71-0.mol
• Article Data: 57

Chemical Properties

• CAS DataBase Reference: 2H-1-Benzopyran-3-carbonitrile, 2-imino-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-1-Benzopyran-3-carbonitrile, 2-imino-(36937-71-0)
• EPA Substance Registry System: 2H-1-Benzopyran-3-carbonitrile, 2-imino-(36937-71-0)

Safety Data

• Hazardous Substances Data: 36937-71-0(Hazardous Substances Data)

Upstream product

• 90-02-8 salicylaldehyde 
• 109-77-3 malononitrile 
• 868-85-9 Dimethyl phosphite 
• 122-52-1 triethyl phosphite 
• 89-95-2 2-methyl-benzyl alcohol 
• 100-52-7 benzaldehyde 

Relevant articles and documents

Design, synthesis, antibacterial, and antifungal studies of novel 3-substituted coumarinyl-triazine derivatives

A series of novel 3-substituted coumarinyltriazine derivatives were designed and synthesized from 3-carboxycoumarins via consecutive Knoevenagel and Pinner reactions in water. All synthesized compounds were characterized by IR, 1 H NMR, 13 C NMR, MS, and elemental analysis. Further, in vitro screening was carried out against four bacterial strains ( Staphylococcus aureus, Bacillus subtilis, Escherichia coli , and Salmonella typhi ) and two fungal strains ( Aspergillus niger and Aspergillus clavatus ).

One-pot four-component approach for the construction of dihydropyridines and dihydropyridinones using amines and activated alkynes

An efficient greener approach for the one-pot four-component synthesis of dihydropyridines has been developed utilizing l-proline as a base catalyst under solvent-free conditions. This domino reaction involves Huisgen dipolar additions using amines and activated alkynes for the formation of novel dihydropyridines. The synthesized dihydropyridines were subjected to acid treatment which resulted in the selective formation of dihydropyridinones as a single diastereomer.

Convenient synthesis of substituted 2-(2-iminocoumarin-3-yl)-thieno[2,3-d] pyrimidin-4-ones

(Chemical Equation Presented) The interaction of both 2-iminocoumarin-3- carbonitriles and 2-iminocoumarin-3-carbothioamides with 2-aminothiophen-3- carboxamides lead to formation of 3-(4-oxo-3,4-dihydrothieno [2,3-d]pyrimidin-2-yl)-2-iminocoumarins in tw

Michael addition of α-azido ketones on iminocoumarin derivatives: An efficient access to new functionalized azido chromenes

A facile one-pot synthesis of functionalized azido chromenes was achieved by Michael addition of α-azido ketones on iminocoumarin derivatives obtained from salicylaldehydes and malononitrile. Synthesized azido chromenes were successfully transformed into

A room temperature one-pot Knoevenagel-Chan-Evans-Lam coupling reaction for synthesis of N-aryl-2-Iminocoumarins in bio-mass-derived green solvent 2-methylTHF

An efficient approach for the synthesis of biologically interesting N-aryl-2-iminocoumarins by a copper-catalyzed one-pot procedure has been developed by the reaction of 2-hydroxybenzaldehydes, malononitrile and arylboronic acids using triethylamine as a base in a bio-mass-derived green solvent 2-MethylTHF at room temperature. This protocol allows access to several N-aryl-2-iminocoumarins in high yields in a relatively short period of time under mild reaction conditions. The procedure operates by a simple telescoped process wherein 2-imino-2H-chromene-3-carbonitriles are formed in situ by the reaction of 2-hydroxybenzaldehyde, malononitrile, and TEA. Further a subsequent one-pot reaction of imine with the arylboronic afforded the target compounds. To understand the reaction mechanism, MALDI-ESI studies were performed, which showed the in situ generated iminocoumarins to be in ligation cooper to form a copper-iminocoumarin complex thus facilitating the smooth formation of N-aryl-2-iminocoumarins in the reaction. Overall, this protocol is practically valuable, useful in organic synthesis, shows good functional group tolerance and provides access to a diverse array of N-aryl-2-iminocoumarins derivatives.

Enantioselective synthesis of 2-amino-4-(nitromethyl)-4H-chromene-3-carbonitriles from 2-iminochromenes

A series of medicinally important 2-amino-4-(nitromethyl)-4H-chromene-3-carbonitriles were synthesized using enantioselective conjugate addition of nitromethane to 2-iminochromenes. The reactions were performed using L8-Cu (II) catalytic system and moderate to good enantioselectivities (62–88%) and yields (66–96%) were obtained.

Polymer supported reagents: Novel methodology for selective and general synthesis of iminocoumarins

A selective synthesis of iminocoumarins 3 was accomplished, starting from salicylaldehydes 1 and nitriles 2, by the use of Amberlite IRA 900 resin as a polymeric solid support. The possibility of using various arylacetonitriles enhances the synthetic vers

Convenient one-step synthesis of a medicinally relevant benzopyranopyridine system

Benzopyrano[2,3-b]pyridine is an important privileged medicinal scaffold. A three-component reaction of salicylaldehydes, thiols and 2 equiv of malononitrile that leads to the formation of a series of compounds incorporating 2,4-diamino-3-cyano-5-sulfanyl

An efficient CuO/rGO/TiO2 photocatalyst for the synthesis of benzopyranopyrimidine compounds under visible light irradiation

In this study, we report on the preparation of a copper oxide/reduced graphene oxide/titanium dioxide (CuO/rGO/TiO2) photocatalyst and its application in a coupling reaction for carbon-nitrogen bond formation under visible light irradiation. The CuO/rGO/TiO2 nanocomposite was synthesized from graphene oxide, Cu and Ti precursors and was fully characterized by scanning electron microscopy (SEM), energy dispersive spectroscopy (EDS), inductively coupled plasma optical emission spectroscopy (ICP-OES), X-ray diffraction (XRD), Fourier-transform infrared (FT-IR) spectroscopy, X-ray photoelectron spectroscopy (XPS), high resolution transmission electron microscopy (HRTEM), cyclic voltammetry (CV), UV-vis absorption, and photoluminescence (PL) spectroscopy. The photocatalytic effectiveness of the CuO/rGO/TiO2 nanocomposite was explored in a pseudo 4-component reaction of salicylaldehyde, malononitrile and secondary amines for the preparation of benzopyranopyrimidines in high yields (75-95%) under visible light irradiation (60-120 min) in ethanol as the solvent at room temperature. Furthermore, the photocatalytic activity of the CuO/rGO/TiO2 nanocomposite was studied in a domino reaction for the coupling of salicylaldehyde and malononitrile in the presence of other aldehydes and secondary amines under the same reaction conditions to afford the corresponding benzopyranopyrimidine derivatives in 77-93% yields after 120-180 min. The reusability investigation of the CuO/rGO/TiO2 photocatalyst showed that it could be recovered and recycled for 5 runs without a significant decrease in its catalytic activity.

Tantalum vs Niobium MCF nanocatalysts in the green synthesis of chromene derivatives

TaMCF silicas modified with alkaline metals can be considered a novel family of highly efficient bifunctional catalysts involved in the synthesis of chromene derivatives, from salicylaldehyde 2 and acetonitrile compounds, under mild conditions, showing enhanced catalytic performance than their NbMCF analogues. The observed reactivity was mainly attributed to the higher basicity of the Me/TaMCF but also the texture of the samples. The Me/TaMCF silicas showed higher Br?nsted basicity than the Nb ones as indicated by the stronger interaction between alkali metals and Ta in the UV–vis and the test reaction experiments. On the other hand, the basicity of Me/TaMCF together the reactivity degree and steric hindrance of the starting acetonitriles are key factors influencing the reaction selectivity. In conclusion, the basicity of the samples plays an important role initiating the reaction by activation of nucleophile but also a compromise between alkaline cation size and basicity is required.

Enantioselective vinylogous Michael addition of β,γ-unsaturated butenolide to 2-iminochromenes

An efficient organocatalyzed asymmetric synthesis of 2-amino-4-(2-furanone)-4H-chromene-3-carbonitriles via vinylogous Michael addition of non-activated β,γ-unsaturated butenolide to 2-iminochromenes has been realized.