87748-33-2Relevant articles and documents
Chemoselective Nitrosylation of Anilines and Alkynes via Fragmentary or Complete NO Incorporation
Pan, Jun,Li, Xinyao,Lin, Fengguirong,Liu, Jianzhong,Jiao, Ning
, p. 1427 - 1442 (2018)
The cycloaddition reactions have been explored extensively and provided an efficient strategy for the synthesis of cyclic compounds. Traditionally, the reaction partners were in extenso incorporated into the cyclic products without fragmentation. From a different perspective, if certain fragmentations via chemical-bond cleavage are involved in this cycloaddition reaction, it would change the assembly sequence and enable more product diversity. Here, we report a chemoselective nitrosylation of anilines and alkynes through fragmentary or complete NO radical incorporation. The formation of multiple C–N bonds, an unexpected C–N bond, and N=O bond cleavage make this fragmentary cycloaddition reaction an efficient approach to 2,5-dihydrooxazoles, 1H-1,2,3-triazole 2-oxides or quinoxaline N-oxides. Facile operation in open-air, metal-free, and mild conditions renders this protocol particularly practical and attractive. A series of mechanistic studies and density functional theory calculations were also conducted, which help to explain the fragmentary or complete NO incorporation processes, broadening the field of new reaction discovery. Exploring novel structures and developing convenient and direct methods to achieve them are an essential issue in synthetic chemistry. In traditional cycloaddition reactions, the reaction partners are in extenso incorporated into the cyclic compound products. In contrast, the fragmentary incorporation of the reaction partners via chemical-bond cleavage in cycloaddition reactions would change the assembly sequence and enable more product diversity. However, fragmentary incorporation in cycloaddition reactions remains a challenging issue because of the high bond-dissociation energy and poor selectivity. This paper reports a fragmentary cycloaddition reaction that enables a series of new structures through a controllable radical process. This work also reveals the diversity of transformation of free radical intermediates. The accessible products might also trigger some interest in pharmaceutical science and materials science. Cycloaddition reactions provide an efficient strategy for the synthesis of cyclic compounds and have been well developed. However, cycloaddition reactions with fragmentary partner incorporation via the cleavage of multiple bonds, which allows for more structural diversity than traditional cycloaddition reactions, have seldom been reported. Here, we describe a chemoselective nitrosylation of anilines and alkynes through fragmentary or complete NO radical incorporation for an efficient approach to 2,5-dihydrooxazoles, 1H-1,2,3-triazole 2-oxides, or quinoxaline N-oxides.
Synthesis, crystal structure and dft studies of polyfunctionalized alkenes: A transition metal-free c(sp2)-h sulfenylation of electron deficient alkyne
Khurana, J. M.,Kumar, Parvin,Saroha, Mohit,Sindhu, Jayant
, (2020/08/24)
An efficient, novel and transition metal-free protocol has been developed for the synthesis of polyfunctionalized aminothioalkenes via direct C[sbnd]H sulfenylation of in situ generated enamines. The reaction was performed using a catalytic amount of inex
One-Pot Synthesis of Benzo[4,5]imidazo[1,2-a]pyrimidin-2-ones Using a Hybrid Catalyst Supported on Magnetic Nanoparticles in Green Solvents
Moussa, Alkassoume,Rahmati, Abbas
, p. 764 - 774 (2021/08/30)
The conversion of soluble polyoxometalate into insoluble polyoxometalate is considered to be one of the major challenges in synthetic organic chemistry. Here, polyoxometalate was bonded to the salt part of an organic branch immobilized on the silica-coate
Novel One-Pot Synthesis of Functionalized Quinolines from Isocyanides, Aniline, and Acetylene Dicarboxylate via Cu-Catalyzed Intramolecular C─H Activation Reactions
Nematpour, Manijeh,Rezaee, Elham,Jahani, Mehdi,Tabatabai, Sayyed Abbas
, p. 1254 - 1259 (2019/03/07)
The one-pot synthesis of a novel class of substituted quinoline derivatives with good yields is achieved via the Cu-catalyzed intramolecular C─H activation reaction between isocyanides, aniline, and acetylene dicarboxylate in MeCN at room temperature. The
Application and developing of iron-doped multi-walled carbon nanotubes (Fe/MWCNTs) as an efficient and reusable heterogeneous nanocatalyst in the synthesis of heterocyclic compounds
Sharghi, Hashem,Aboonajmi, Jasem,Mozaffari, Mozhdeh,Doroodmand, Mohammad Mahdi,Aberi, Mahdi
, (2017/11/16)
Iron-doped multi-walled carbon nanotubes (Fe/MWCNTs) is an efficient, ecofriendly and reusable heterogeneous nanocatalyst for the one-pot synthesis of heterocyclic compounds including bis-spiro piperidines, piperidines, dihydro-2-oxopyrroles, pyrazoles and diazepines at room temperature with good to excellent yields. The heterogeneous nanocatalyst was fully characterized by scanning electron microscopy (SEM), X-ray diffraction (XRD), inductively coupled plasma (ICP) and FT-IR analysis. Also, the structures of all prepared compounds were characterized by 1H NMR, 13C NMR, FT-IR, mass spectrometry (MS) and elemental analysis. The major advantages of these protocols are mild and green reaction conditions, short reaction times, clean reaction, operational simplicity, easy purification and good to excellent yields with the reusable heterogeneous nanocatalyst. The catalyst was ten recycled without significant loss of activity.
Trifluoroacetic acid catalyzed one-pot four-component domino reaction for the synthesis of substituted dihydro 2-oxypyrroles
Lashkari, Mojtaba,Maghsoodlou, Malek Taher,Karima, Mahsa,Kangani, Mehrnoosh
, p. 3799 - 3802 (2018/05/24)
Trifluoroacetic acid was applied as an effcient catalyst for the one-pot four-component synthesis of N-aryl/alkyl-3-aminodihydropyrrol-2-one-4-carboxylates via the domino reaction of amines, formaldehyde and dialkyl acetylenedicarboxylates at ambient temp
A three-component one-pot synthesis of penta-substituted pyrroles via ring opening of α-nitroepoxides
Zhao, Donghong,Zhu, Yue,Guo, Shanshan,Chen, Wenteng,Zhang, Guolin,Yu, Yongping
supporting information, p. 2872 - 2877 (2017/04/26)
A novel and facile one-pot reaction has been developed to synthesize a variety of penta-substituted pyrroles from α-nitroepoxides, primary amines and dialkyl acetylenedicarboxylates under the conditions without catalyst. Furthermore, the controlled experi
Iodine/Copper Iodide-Mediated C-H Functionalization: Synthesis of Imidazo[1,2-a]pyridines and Indoles from N-Aryl Enamines
Liu, Jing,Wei, Wei,Zhao, Ting,Liu, Xuanyu,Wu, Jie,Yu, Wenquan,Chang, Junbiao
, p. 9326 - 9336 (2016/10/14)
A practical intramolecular C-H functionalization reaction of N-aryl enamines has been carried out with molecular iodine (I2) as the sole oxidant in the presence of copper iodide (CuI). The efficient and versatile synthetic method described here
Synthesis of fused pyrrolo[3,4-d]tetrahydropyrimidine derivatives by proline-catalyzed multicomponent reaction
Chen, Zhi-Peng,Wang, Hai-Bo,Wang, Yu-Qin,Zhu, Qiu-Hua,Xie, Yang,Liu, Shu-Wen
supporting information, p. 4379 - 4385 (2014/06/10)
Novel proline-catalyzed multicomponent reactions (MCRs) for the synthesis of fused pyrrolo[3,4-d]tetrahydropyrimidines 7 and 9 with different substituted patterns have been developed, which provide rapid access to a library of compounds 7 and 9 in medium to excellent yields, by using N-methyl-α- aryl(alkyl)aminomaleimides, amines, and aldehydes as reactants. The catalyst and the ratio of reactants were found to have significant impact on these reactions, and a reasonable mechanism was also proposed.
A one-pot multi-component synthesis of N-aryl-3-aminodihydropyrrol-2-one-4- carboxylates catalysed by oxalic acid dihydrate
Sajadikhah, Seyed Sajad,Hazeri, Nourallah,Maghsoodlou, Malek Taher,Mostafa, Sayyed,Habibi-Khorassani,Khandan-Barani, Khatereh
, p. 40 - 42 (2013/04/10)
A simple synthesis of N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates via one-pot multi-component reaction of amines, dialkyl acetylenedicarboxylates and formaldehyde in the presence of oxalic acid dihydrate (20 mol%) as catalyst in methanol is described
