4651-92-7

Usage

Physical State

Yellowish, crystalline solid

Functional Groups

Amino group ( -\textNH2 )
Ethyl group ( -\textC2\textH5 )
Methyl group ( -\textCH3 )
Thiophene ring
Nitrile group ( -\textCN )

Applications

Intermediate in pharmaceutical synthesis
Intermediate in agrochemical synthesis
Building block for complex organic molecules

Utility

Reacts with other compounds to form complex organic molecules

Potential Applications

Medicinal chemistry
Material science

InChI:InChI=1/C8H10N2S/c1-3-6-5(2)11-8(10)7(6)4-9/h3,10H2,1-2H3

Upstream product

• 96-22-0 pentan-3-one 
• 109-77-3 malononitrile 

Downstream Products

• 439692-89-4 5-ethyl-6-methylthieno[2,3-d]pyrimidin-4(3H)-one 
• 439692-90-7 4-chloro-5-ethyl-6-methylthiopheno[2,3-d]pyrimidine 

Relevant academic research and scientific papers

Facile pathway for synthesis of two efficient catalysts for preparation of 2-aminothiophenes and tetrahydrobenzo[b]pyrans

Abstract: We report here a new magnetically recyclable catalyst consisting of iron-substituted Keggin-type heteropolyacid (HPA) grafted on modified Fe3O4 nanoparticles. The synthesized hybrid nanomaterial exhibited the excellent catalytic efficiency in condensation reaction for the preparation of tetrahydrobenzo[b]pyrans under solvent-free conditions as well as in the synthesis of 2-aminothiophenes via Gewald reaction. It must be noted that, HPA supported magnetite nanoparticles catalyzed the preparation of tetrahydrobenzo[b]pyrans, whereas for Gewald reaction amine-functionalized magnetite nanoparticles acted as a catalyst. Different characterization techniques such as Fourier transform infrared (FT-IR), X-ray powder diffraction (XRD), field emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM) and vibrating sample magnetometer (VSM) were used to characterize the hybrid nanomaterial. The reusability of catalyst was affirmed by using in consecutive runs for five times. Performance of prepared catalyst was compared with the various previously reported catalysts; the newly synthesized catalysts found to be most efficient with regard to reaction time, yield and ease of catalyst separation. Graphical Abstract: [Figure not available: see fulltext.].

Preparation of magnetically recyclable ZnFe2O4 nanoparticles by easy single-step co-precipitation method and their catalytic performance in the synthesis of 2-aminothiophenes

In this work, a new synthetic route for the preparation of ZnFe2O4 nanoparticles through the chemical co-precipitation using Fe2+ and Fe3+ ions in an alkaline solution was developed. The synthesized nanoparticles were characterized by XRD, FTIR, SEM, ICP-MS, DRS, TGA, VSM and elemental analysis. Characterization results confirmed the formation of single ZnFe2O4 phase, with an average particle size of 40?nm and a high saturation magnetization of 34?emu g?1. The prepared material was employed as a catalyst for the synthesis of 2-aminotiophene derivatives through the Gewald reaction. This thermally and chemically stable nanocatalyst is environmentally benign, economical and reusable which can be easily recovered using an external magnet. Therefore, it appears that this methodology can be simply extended for industrial purposes.

Thieno [2, 3-d] pyrimidine compound, preparation method thereof and application thereof

The invention relates to the field of organic synthesis and discloses a thieno [2, 3-d] pyrimidine compound and an application thereof. The structure of the thieno [2, 3-d] pyrimidine compound is shown in a formula (1), wherein R1 and R2 independently rep

TiO2/nanoclinoptilolite as an efficient nanocatalyst in the synthesis of substituted 2-aminothiophenes

TiO2/nanoclinoptilolite (TiO2/NCP) was prepared by the mediation of hexadecyltrimethylammonium (HDTMA) as surfactant and used as an effective heterogeneous nanocatalyst for the preparation of substituted 2-aminotiophenes. The modified HDTMA/NCP was impregnated with titanium(IV) chloride solution followed by calcination at 500?°C for 20?h. The obtained nanocomposite was characterized using Fourier transform infrared spectroscopy, field emission scanning electron microscopy, inductively coupled plasma optical emission spectroscopy and X-ray diffraction. Moreover, the prepared nanocomposite had high stability and recoverability under mild and solvent-free conditions.

Synthesis, structural properties, and pharmacological evaluation of 2-(acylamino)thiophene-3-carboxamides and analogues thereof

We have previously reported the synthesis and the pharmacological characterization of a family of methyl 2-(acylamino)thiophene-3-carboxylates as GABAB positive allosteric modulators active both in vitro and in vivo. In the present work, we des

Bovine serum albumin-catalyzed one-pot synthesis of 2-aminothiophenes via Gewald reaction

A novel bovine serum albumin (BSA)-catalyzed Gewald reaction in one-pot was developed in this work. The influence of reaction conditions including solvent, temperature and catalyst loading was investigated, and 12 multi-substituted 2-aminothiophene derivatives were prepared with moderate to excellent yields. Recycle experiments were designed to demonstrate the reusability of BSA. This novel activity of BSA to catalyze Gewald reaction is of practical significance in expanding the application of biocatalysts.

Easy single-step preparation of ZnO nano-particles by sedimentation method and studying their catalytic performance in the synthesis of 2-aminothiophenes via Gewald reaction

Zinc oxide is a multi-purpose active material with important catalytic applications. In this study, nano-sized ZnO particles were easily synthesized through sedimentation of zinc acetate di-hydrate in absolute ethanol and were characterized by XRD and SEM. The XRD results indicated pure wurtzite structure with the average particle size of 26.9 nm for the nano-particles. It was observed that size of ZnO nano-particles was decreased while solution concentration was increased. This observation would be explained considering enhancing nucleation processes of nano-particles at high concentration of zinc acetate. The prepared nano-particles (2.5 mol%) were used as catalyst for the fast and efficient synthesis of 2-aminothiophenes under solvent free conditions. The three-component mixture of a carbonyl compound, malonodinitrile, and elemental sulfur was converted into the corresponding 2-aminothiophene in moderate to high yields with excellent selectivity.

KG-60-piperazine as a new heterogeneous catalyst for gewald three-component reaction

Piperazine supported on amorphous silica (KG-60-piperazine) as a basic catalyst acts in the Gewald three-component reaction of some aldehydes and ketones with malononitrile as well as ethyl cyanoacetate. The catalyst shows general utility with a variety of starting carbonyl compounds. Moreover, the catalyst can be reused for four additional cycles without significant loss of the activity. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

SUBSTITUTED 4-(SELENOPHEN-2(OR-3)-YLAMINO)PYRIMIDINE COMPOUNDS AND METHODS OF USE THEREOF

Selenophene compounds of formula (I) are described herein. In the compounds of Formula (I), ring A is a 6-membered aromatic fused ring, optionally containing one, two or three nitrogen atoms; a 5-membered heteroaromatic fused ring; or a mono- or bicyclic

A facile and practical one-pot synthesis of multisubstituted 2-aminothiophenes via imidazole-catalyzed Gewald reaction

A simple and efficient procedure was developed for the synthesis of multisubstituted 2-aminothiophene derivatives. In the presence of catalytic amount of imidazole, ketones or aldehydes, dicyanomethane and elemental sulfur were converted into the corresponding 2-aminothiophene derivatives in moderate to high yields in DMF at 60 °C.