349492-08-6

Basic information

• Product Name: 7-amino-6-cyano-5-(4-nitrophenyl)-4-oxo-2-thioxo-5H-pyrano[2,3-d]pyrimidinone
• Synonyms: 7-amino-6-cyano-5-(4-nitrophenyl)-4-oxo-2-thioxo-5H-pyrano[2,3-d]pyrimidinone
• CAS NO: 349492-08-6
• Molecular Weight: 343.323
• Mol File: 349492-08-6.mol

Chemical Properties

• CAS DataBase Reference: 7-amino-6-cyano-5-(4-nitrophenyl)-4-oxo-2-thioxo-5H-pyrano[2,3-d]pyrimidinone(CAS DataBase Reference)
• NIST Chemistry Reference: 7-amino-6-cyano-5-(4-nitrophenyl)-4-oxo-2-thioxo-5H-pyrano[2,3-d]pyrimidinone(349492-08-6)
• EPA Substance Registry System: 7-amino-6-cyano-5-(4-nitrophenyl)-4-oxo-2-thioxo-5H-pyrano[2,3-d]pyrimidinone(349492-08-6)

Safety Data

• Hazardous Substances Data: 349492-08-6(Hazardous Substances Data)

Upstream product

• 67-52-7 BARBITURIC ACID 
• 555-16-8 4-nitrobenzaldehdye 
• 109-77-3 malononitrile 
• 504-17-6 4,6-dihydroxy-2-mercaptopyrimidine 

Relevant articles and documents

SO3H-functionalized nano-MGO-D-NH2: Synthesis, characterization and application for one-pot synthesis of pyrano[2,3-d]pyrimidinone and tetrahydrobenzo[b]pyran derivatives in aqueous media

An SO3H-functionalized nano-MGO-D-NH2 catalyst has been prepared by multi-functionalization of a magnetic graphene oxide (GO) nanohybrid and evaluated in the synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-d]pyrimidinone derivati

4,4'-trimethylenedipiperidine as a nitrogen heterocycle solvent and/or catalyst: Liquid phase tandem Knoevenagel-Michael condensation

Liquid phase tandem Knoevenagel-Michael condensation of various aromatic and heteroaromatic aldehydes with barbituric acid or 2-thiobarbituric acid and malononitrile was studied in a one-pot three-component reaction. For the first time, TMDP was employed as a safe and efficient solvent and/or catalyst in the liquid and aqueous ethanol medium, respectively, for the practical and eco-friendly Knoevenagel-Michael condensation. The reactions were carried out by using greener procedures, including a) the use of TMDP as an N-heterocycle organocatalyst in a green medium including water and ethanol (1:1 v/v) at reflux temperature, and b) the use of TMDP as a dual solvent-catalyst at 65 °C in the absence of any solvent. High to excellent yields of the desired pyrano[2,3-d] pyrimidinones were obtained under the two earlier mentioned conditions. The current methodologies have advantages, including (a) avoiding hazardous, toxic, volatile, and flammable materials and solvents, (b) avoiding tedious processes, harsh conditions, and multiple steps for the preparation of catalysts, (c) using a less toxic and noncorrosive catalyst, (d) minimizing hazardous waste generation and simple workup process, and (e) high recyclability of TMDP. Another important result of this work is that the TMDP can be a promising alternative for toxic, volatile, and flammable base reagents such as piperidine and triethylamine in liquid phase organic syntheses owing to its unique properties such as being less toxic, nonflammable, and nonvolatile, and having a low melting point, broad liquid range temperature, high thermal stability, and safe handling and storage.

SCMNPs@Urea/Py-CuCl2: a recyclable catalyst for the synthesis of pyrano[2,3-d]pyrimidinone and pyrano[2,3-d] pyrimidine-2,4,7-trione derivatives

An efficient, simple, and mild strategy for the one-pot multicomponent synthesis of pyrano[2,3-d]pyrimidinone and pyrano[2,3-d]pyrimidine-2,4,7-trione derivatives is described using SCMNPs@Urea/Py-CuCl2 nanoparticles as a reusable heterogeneous magnetic nanocatalyst. The catalyst was characterized using Fourier transform infrared spectroscopy (FTIR), thermogravimetric analysis (TGA), vibrating sample magnetometry (VSM), energy dispersive X-ray spectroscopy (EDX), X-ray diffraction (XRD), and scanning electron microscopy (SEM). The SCMNPs@Urea/Py-CuCl2 can be easily collected from the reaction solution by magnetic decantation using a permanent magnetic field and reused in six runs without significant decrease in catalytic activity.

A choline chloride-based deep eutectic solvent promoted three-component synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-d] pyrimidinone (thione) derivatives

An efficient one-pot method for the synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-d]pyrimidinone (thione) derivatives through a three-component reaction between aldehydes, malononitrile and enolizable C–H activated acidic compounds using a new deep eutectic solvent made of choline chloride, urea and thiourea as an environmentally benign catalyst has been reported. The structure of the catalyst was characterized using FT-IR, 1H NMR, and 13C NMR. The present method exhibits some notable advantages such as ease of the preparation and handling of the catalyst, low cost, green reaction conditions, short reaction times, high yields, and simple work-up. Also, the catalyst could be recovered easily and recycled up to four times without significant loss of catalytic activity.

Introduction of an efficient DABCO-based bis-dicationic ionic salt catalyst for the synthesis of arylidenemalononitrile, pyran and polyhydroquinoline derivatives

—An affordable DABCO-based bis-dicationic ionic salt ([(DABCO)2C3H5OH]·2Cl) was utilized for the synthesis of arylidenemalononitrile, tetrahydrobenzo[b]pyran, pyrano[2,3-d]-pyrimidinone (thione), dihydropyrano[3,2-c]chrome

Verjuice as a green and bio-degradable solvent/catalyst for facile and eco-friendly synthesis of 5-arylmethylenepyrimidine-2,4,6-trione, pyrano[2,3-d]pyrimidinone and pyrimido[4,5-d]pyrimidinone derivatives

Verjuice (unripe grape juice), a natural mixture of organic acids, which is identified by pH-metric and TGA analysis, is efficiently used for the promotion of the synthesis of 5-arylmethylenepyrimidine-2,4,6-triones, via Knovenagel condensation reaction between barbituric or thiobarbituric acid and aldehydes. Verjuice is also employed for the effective synthesis of pyrano[2,3-d]pyrimidinone derivatives via a three-component reaction of barbituric acid or its thio analogue, aldehydes and malononitrile. In the same way, pyrimido[4,5-d]pyrimidinone derivatives are simply produced via the reaction of barbituric acid, aldehydes and urea or thiourea in the presence of verjuice. This green methodology rewards notable advantages including simple procedures, acceptable reaction times, easy work-up, high yields, circumventing the use of any expensive starting materials, volatile and hazardous organic solvents during the reaction and work-up process, and use of a natural, low-cost, reusable, and bio-degradable catalyst.

Synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-d]pyrimidinone derivatives using Fe3O4@Ph-PMO-NaHSO4 as a new magnetically separable nanocatalyst

Immobilized NaHSO4 on core/shell phenylene bridged periodic mesoporous organosilica magnetic nanoparticles (Fe3O4@Ph-PMO-NaHSO4) as a new acidic magnetically separable nanocatalyst was successfully prepared in three steps: (i) preparation of Fe3O4 nanoparticles by a precipitation method, (ii) synthesis of an organic-inorganic periodic mesoporous organosilica structure with phenyl groups on the surface of Fe3O4 magnetic nanoparticles (MNPs) and (iii) finally adsorption of NaHSO4 on periodic mesoporous organosilica (PMO) network. The prepared organic-inorganic magnetic reagent was characterized by Fourier transform infrared spectroscopy (FT-IR), X-ray powder diffraction (XRD), transmission electron microscopy (TEM), N2 adsorption-desorption and energy-dispersive X-ray (EDX) techniques. Finally, it was used as a reusable and new catalyst to promote the synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-d]pyrimidinone derivatives as important biologically active compounds. Eco-friendly protocol, high yields, short reaction times and easy and quick isolation of the products are the main advantages of this procedure.

Preparation of a new DABCO-based ionic liquid [H2-DABCO][H2PO4]2} and its application in the synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-d]pyrimidinone derivatives

A new acidic ionic liquid, 1,4-diazabicyclo[2.2.2]octane-1,4-diium dihydrogen phosphate {[H2-DABCO][H2PO4]2}, was prepared in a quick and straightforward process and characterized by using different methods such as FT-IR, NMR and Mass analysis. Then it was used as a reusable and new catalyst to promote the synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-d]pyrimidinone derivatives as important biologically active compounds that they are used in pharmaceutical industry. This adequate procedure possess some advantages like producing target compounds in high yields, short reaction times, simple work-up procedure and use of chief and easily preparable catalyst.

Green cellulose-based nanocomposite catalyst: Design and facile performance in aqueous synthesis of pyranopyrimidines and pyrazolopyranopyrimidines

A cellulose-based nanobiocomposite decorated with Fe3O4 nanoparticles was prepared, characterized and applied as an easily recoverable and reusable green nanocatalyst in the synthesis of pyrano[2,3-d]pyrimidine derivatives in water a

DABCO-based ionic liquids: Green and recyclable catalysts for the synthesis of barbituric and thiobarbituric acid derivatives in aqueous media

A new and straightforward method for the synthesis of 5-arylidine barbituric and thiobarbituric acids through a reaction between barbituric acid and its thio-analogue with aldehydes using 1,4-disulfo-1,4-diazabicyclo[2.2.2]octane-1,4-diium dihydrogen sulfate ([DABCO](SO3H)2(HSO4)2) as an efficient catalyst has been reported. In this project, also the preparation of pyrano[2,3-d]-pyrimidinediones via the reaction of barbituric or thiobarbituric acid, malononitrile and aldehydes in the presence of this reagent and 1,4-disulfo-1,4-diazabicyclo[2.2.2]octane-1,4-diium chloride ([DABCO](SO3H)2(Cl)2) has been investigated. The structure of the products was characterized using IR, 1H NMR and 13C NMR spectroscopy. The present methodologies suggests several advantages such as ease of the preparation and handling of the catalysts, high yields, simple and green procedures, low cost, short reaction times, easy work-up and preformation of the reaction in water as a green solvent.