4265-16-1Relevant articles and documents
The potential rewarding and reinforcing effects of the substituted benzofurans 2-EAPB and 5-EAPB in rodents
Sayson, Leandro Val,Custodio, Raly James Perez,Ortiz, Darlene Mae,Lee, Hyun Jun,Kim, Mikyung,Jeong, Youngdo,Lee, Yong Sup,Kim, Hee Jin,Cheong, Jae Hoon
, (2020)
Accounts regarding the use of novel psychoactive substances continue to escalate annually. These include reports on substituted benzofurans (SBs), such as 1-(1-benzofuran-2-yl)-N-ethylpropan-2-amine (2-EAPB) and 1-(1-benzofuran-5-yl)-N-ethylpropan-2-amine (5-EAPB). Reports on the deaths and adverse consequences from the use of SBs warrant the investigation of their mechanism, possibly predicting the effects of similar compounds. Accordingly, we investigated the possible rewarding and reinforcing effects of 2-EAPB and 5-EAPB through conditioned place preference (CPP), self-administration, and locomotor sensitization tests. We also determined the possible influence of 2-EAPB and 5-EAPB administration on dopamine- and plasticity-related proteins in the nucleus accumbens and ventral tegmental area. 2-EAPB and 5-EAPB induced CPP at different doses and were self-administered by rats. Only 5-EAPB induced locomotor sensitization in mice. 2-EAPB and 5-EAPB did not alter the expressions of dopamine D1 and D2 receptors in the nucleus accumbens, nor changed tyrosine hydroxylase and dopamine transporter expressions in the ventral tegmental area. Both 2-EAPB and 5-EAPB enhanced deltaFosB, but not transcription factor cyclic AMP-response-element binding protein and brain-derived neurotrophic factor in the nucleus accumbens. Hence, the potential rewarding and reinforcing effects on rodents induced by 2-EAPB and 5-EAPB may possibly be associated with alterations in other neurotransmitter systems (besides mesolimbic) and/or neuro-plastic modifications.
Synthesis of new Zn (II) complexes for photo decomposition of organic dye pollutants, industrial wastewater and photo-oxidation of methyl arenes under visible-light
Ahemed, Jakeer,Bhongiri, Yadagiri,Chetti, Prabhakar,Gade, Ramesh,Kore, Ranjith,Pasha, Jakeer,Pola, Someshwar,Rao D, Venkateshwar
, (2021/07/28)
Synthesis of new Schiff's base Zn-complexes for photo-oxidation of methyl arenes and xylenes are reported under visible light irradiation conditions. All the synthesized new ligands and Zn-complexes are thoroughly characterized with various spectral analyses and confirmed as 1:1 ratio of Zn and ligand with distorted octahedral structure. The bandgap energies of the ligands are higher than its Zn-complexes. These synthesized new Zn(II) complexes are used for the photo-fragmentation of organic dye pollutants, photodegradation of food industrial wastewater and oxidation of methyl arenes which are converted into its respective aldehydes with moderate yields under visible light irradiation. The photooxidation reaction dependency on the intensity of the visible light was also studied. With the increase in the dosage of photocatalyst, the methyl groups are oxidized to get aldehydes and mono acid products, which are also identified from LC-MS data. Finally, [Zn(PPMHT)Cl] is with better efficiency than [Zn(PTHMT)Cl] and [Zn(MIMHPT)Cl] for oxidation of methyl arenes is reported under visible-light-driven conditions.
Rh-Catalyzed Formal [3+2] Cyclization for the Synthesis of 5-Aryl-2-(quinolin-2-yl)oxazoles and Its Applications in Metal Ions Probes
Zhou, Tongtong,He, Xinwei,Zuo, Youpeng,Wu, Yuhao,Hu, Wangcheng,Zhang, Shiwen,Duan, Jiahui,Shang, Yongjia
, p. 621 - 626 (2021/02/12)
A facile and efficient strategy for the synthesis of 5-aryl-2-(quinolin-2-yl)oxazoles via rhodium-catalyzed formal [3+2] cyclization of 4-aryl-1-tosyl-1H-1,2,3-triazoles with quinoline-2-carbaldehydes has been described. The protocol employs mild conditions and offers good yields of diverse 2,5-aryloxazole derivatives with a broad reaction scope. It is amenable to gram-scale synthesis and easily transformation. Moreover, this 5-aryl-2-(quinolin-2-yl)oxazole skeleton is indeed a new fluorophore and its applications in metal ions probes are also investigated and showed fluorescent responses to mercury ion.
Efficient synthesis of acrylates bearing an aryl or heteroaryl moiety: One-pot method from aromatics and heteroaromatics using formylation and the horner-wadsworth-emmons reaction
Yasukata, Tatsuro,Matsuura, Takaharu
, p. 527 - 533 (2021/03/22)
Acrylates bearing an aryl or heteroaryl moiety were efficiently prepared by a one-pot process employing a sequence of lithiation, formylation and the Horner-Wadsworth-Emmons reaction starting from aromatic and heteroaromatic compounds. This method can efficiently introduce an acrylate moiety into aromatic and heteroaromatic compounds.
Synthesis of multi-substituted 1,2,4-triazoles utilising the ambiphilic reactivity of hydrazones
Matsuzaki, Haruo,Takeda, Norihiko,Yasui, Motohiro,Okazaki, Mayuko,Suzuki, Seishin,Ueda, Masafumi
, p. 12187 - 12190 (2021/11/30)
The synthesis of N-alkyl-1H-1,2,4-triazoles from N,N-dialkylhydrazones and nitriles via formal [3+2] cycloaddition including the C-chlorination/nucleophilic addition/cyclisation/dealkylation sequence was developed. This sequential reaction utilising the in situ generation of hydrazonoyl chloride based on the ambiphilic reactivity of hydrazones afforded a variety of multi-substituted N-alkyl-triazoles in high yields. The synthetic utility of multi-substituted triazoles was also demonstrated by further transformations.
METAL-FREE SOLVENT-FREE SYNTHESIS OF FUSED-PYRIDO HETEROCYCLES AND BIOMEDICAL APPLICATIONS
-
Paragraph 0085; 00110; 00112, (2021/01/29)
Embodiments herein provide fused-pyrido heterocycles such as azaindoles, carboline derivatives, furo[b]pyridines or furo[b]pyridine-isatin hybrids of Formula I. Embodiments also relate to a process for a synthesis of variety of complex pyrido-heterocycles The pyrido-heterocycles can be used for treating cancer (cervix, kidney, lung, breast and epidermal skin) and multi-drug resistant tuberculosis. These heterocycles can also be used as anti-biofilm agents against pathogenic strains, which will minimize the risk of secondary infections.
Photo-on-Demand Synthesis of Vilsmeier Reagents with Chloroform and Their Applications to One-Pot Organic Syntheses
Liang, Fengying,Eda, Kazuo,Okazoe, Takashi,Wada, Akihiro,Mori, Nobuaki,Konishi, Katsuhiko,Tsuda, Akihiko
, p. 6504 - 6517 (2021/05/06)
The Vilsmeier reagent (VR), first reported a century ago, is a versatile reagent in a variety of organic reactions. It is used extensively in formylation reactions. However, the synthesis of VR generally requires highly toxic and corrosive reagents such as POCl3, SOCl2, or COCl2. In this study, we found that VR is readily obtained from a CHCl3 solution containing N,N-dimethylformamide or N,N-dimethylacetamide upon photo-irradiation under O2 bubbling. The corresponding Vilsmeier reagents were obtained in high yields with the generation of gaseous HCl and CO2 as byproducts to allow their isolations as crystalline solid products amenable to analysis by X-ray crystallography. With the advantage of using CHCl3, which bifunctionally serves as a reactant and a solvent, this photo-on-demand VR synthesis is available for one-pot syntheses of aldehydes, acid chlorides, formates, ketones, esters, and amides.
Nickel-Catalyzed Amination of α-Aryl Methyl Ethers
Patel, Purvish,Rousseaux, Sophie A. L.
, p. 492 - 496 (2020/03/13)
α-Aryl amines are prevalent in pharmaceutically active compounds and natural products. Herein, we describe a Ni-catalyzed protocol for their synthesis from readily available α-aryl ethers. While α-aryl ethers have been used as electrophiles in Ni-catalyzed C-C bond formations, their use in C-heteroatom bond formation is much less prevalent. Preliminary mechanistic insight suggests that oxidative addition is facilitated by an anionic ligand and that reductive elimination is a reversible process.
Discovery of orthogonal synthesis using artificial intelligence: Pd(OAc)2-catalyzed one-pot synthesis of benzofuran and bicyclo[3.3.1]nonane scaffolds
Takabatake, Tetsuhiko,Fujiwara, Keisuke,Okamoto, Sho,Kishimoto, Ryo,Kagawa, Natsuko,Toyota, Masahiro
, (2020/08/10)
A synthetic route for the common intermediate, methyl 2-formylbenzofuran-7-carboxylate (7a), to efficiently assemble three bioactive benzofurans 4–6 was explored using the artificial intelligence system SYNSUP. Among the routes proposed by SYNSUP, we investigated a three-step synthesis of 7a using methyl 4-ally-3-oxohept-6-enoate (10). A new catalytic reaction was found in which 7a was directly obtained from 10 in a single step with a yield of 24percent. It was found that this chemical yield could be increased to 74percent when methyl 3-allyl-2-hydroxybenzoate (9a), an intermediate of the above one-pot transformation, was subjected to the catalytic process. In addition, in this catalytic process, 8a (76percent) and 11 (77percent) were each selectively synthesized from 10 by changing only the solvent. Therefore, we created a novel orthogonal synthesis of methyl 2-methylbenzofuran-7-carboxylate (8a) and methyl 9-oxobicyclo[3.3.1]nona-3,6-diene-1-carboxylate (11). Finally, the total syntheses of bioactive benzofurans 4–6 were completed smoothly using 7a and 8a.
From Benzofurans to Indoles: Palladium-Catalyzed Reductive Ring-Opening and Closure via β-Phenoxide Elimination
Perego, Luca A.,Wagschal, Simon,Grüber, Raymond,Fleurat-Lessard, Paul,El Ka?m, Laurent,Grimaud, Laurence
supporting information, p. 151 - 159 (2018/12/05)
Benzofurans can undergo ring-opening by a palladium-catalyzed process resulting in C?O bond breaking. Benzofuran-tethered 2-iodoanilines give synthetically interesting 2-(3-indolylmethyl)phenols in an overall reductive process. Mechanistic studies suggest that this unusual reaction proceeds by carbopalladation of benzofuran giving a 3-palladated 2,3-dihydrobenzofuran intermediate, which then fragments by an uncommon trans-elimination of the phenoxide group β to the metal. In this transformation, N,N-diisopropylethylamine (DIPEA) acts as a base and as a reducing agent: it regenerates palladium(0) from palladium(II), thus allowing catalytic turnover. (Figure presented.).
