17216-62-5Relevant academic research and scientific papers
Intramolecular Schmidt reaction of acyl chlorides with alkyl azides: Preparation of pyrrolizine by intramolecular capture of intermediates with alkenes or alkynes
Wang, Bao-Juan,Xue, Ping,Gu, Peiming
, p. 2277 - 2279 (2015)
The preparation of substituted pyrrolizines through the Schmidt reaction of acyl chlorides with alkyl azides has been realized. Intramolecular capture of the isocyanate ion and N-acyliminium ion intermediates from the Schmidt process with alkene or alkyne
Iron-Catalyzed Tertiary Alkylation of Terminal Alkynes with 1,3-Diesters via a Functionalized Alkyl Radical
Tian, Ming-Qing,Shen, Zhen-Yao,Zhao, Xuefei,Walsh, Patrick J.,Hu, Xu-Hong
supporting information, p. 9706 - 9711 (2021/03/19)
Direct oxidative C(sp)?H/C(sp3)?H cross-coupling offers an ideal and environmentally benign protocol for C(sp)?C(sp3) bond formations. As such, reactivity and site-selectivity with respect to C(sp3)?H bond cleavage have remained a persistent challenge. Herein is reported a simple method for iron-catalyzed/silver-mediated tertiary alkylation of terminal alkynes with readily available and versatile 1,3-dicarbonyl compounds. The reaction is suitable for an array of substrates and proceeds in a highly selective manner even employing alkanes containing other tertiary, benzylic, and C(sp3)?H bonds alpha to heteroatoms. Elaboration of the products enables the synthesis of a series of versatile building blocks. Control experiments implicate the in situ generation of a tertiary carbon-centered radical species.
DIASTEREOMERIC LINKING REAGENTS FOR NUCLEOTIDE PROBES
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Paragraph 94-97, (2021/04/02)
A versatile reagent with a non-nucleotide monomeric unit comprising an enantiomeric center and having a ligand, and first and second coupling groups that are linked to the non-nucleotide monomeric unit. Such a reagent permits preparation of versatile nucleotide/non-nucleotide polymers, having any desired sequence of nucleotide and non-nucleotide monomeric units, each of the latter of which bear a desired ligand. These polymers can, for example, be used as probes which can exhibit enhanced sensitivity and/or which are capable of detecting a genus of nucleotides each species of which has a common target nucleotide sequence of interest bridged by different sequences not of interest.
Schmidt Reaction of ω-Azido Valeryl Chlorides Followed by Intermolecular Trapping of the Rearrangement Ions: Synthesis of Assoanine and Related Pyrrolophenanthridine Alkaloids
DIng, Shao-Lei,Ji, Yang,Su, Yan,Li, Rui,Gu, Peiming
, p. 2012 - 2021 (2019/02/14)
The Schmidt reaction of ω-azido valeryl chlorides in the presence of an additional nucleophile was explored. The arenes, alcohols, and amines were demonstrated as the intermolecular trapping reagents for isocyanate ion and N-acyliminium ion from the Schmidt rearrangement, affording the corresponding products with moderate to excellent yields. Two 2-oxoindoles from the reaction were successfully converted into four natural alkaloids, namely, assoanine, anhydrolycorine, oxoassoanine, and anhydrolycorinone.
2 - Oxygen -3 - piperidine carboxylic acid ethyl ester preparation method (by machine translation)
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Paragraph 0025; 0026; 0029; 0030; 0031, (2018/09/21)
The invention provides a 2 - oxo - 3 - piperidine carboxylic acid ethyl ester preparation method, comprising the following steps: S1, the malonic acid diethyl ester and alkaline catalyst after mixing, in the 10 - 50 °C dropping acrylonitrile, obtained by reaction of 2 - cyanoethyl malonic acid diethyl ester; S2, will be the 2 - cyanoethyl malonic acid diethyl ester and organic solvent, [...] catalyst in the hydrogen environment, for 75 - 130 °C react under the, recrystallization to obtain the 2 - oxo - 3 - piperidine carboxylic acid ethyl ester. Compared with the prior art, this invention has the following advantages: the present invention provides a 2 - oxo - 3 - piperidine ethyl formate manufacturing method, with raw materials are easy, simple operation, total yield compared with the classic N·F·Albertsm method up to 77% above (improved 20%), so it is very suitable for industrial production. (by machine translation)
On-water magnetic NiFe2O4 nanoparticle-catalyzed Michael additions of active methylene compounds, aromatic/aliphatic amines, alcohols and thiols to conjugated alkenes
Payra, Soumen,Saha, Arijit,Banerjee, Subhash
, p. 95951 - 95956 (2016/10/25)
Here, we have demonstrated the Michael addition of active methylene compounds, aromatic/aliphatic amines, thiols and alcohols to conjugated alkenes using magnetic nano-NiFe2O4 as reusable catalyst in water. Nano-NiFe2O4 efficiently catalyzed the formation of C-C and C-X (X = N, S, O etc.) bond through 1,4-addition reactions.
Rapid synthesis of substituted pyrrolines and pyrrolidines by nucleophilic ring closure at activated oximes
Chandan, Nandkishor,Thompson, Amber L.,Moloney, Mark G.
supporting information, p. 7863 - 7868 (2013/07/05)
Substituted pyrrolines are available by ring closure initiated by direct nucleophilic attack of stabilized enolates at the nitrogen of oximes activated with a leaving group, in a process which effectively out-competes the more usual Beckmann rearrangement. Subsequent reduction provides diastereoselective access to the corresponding pyrrolidines. This provides a rapid route to saturated heterocyclic systems from readily available precursors.
Michael addition approach for the synthesis of novel spiro compounds and 2-substituted malonic acid derivatives from Meldrum's acid
Chande, Madhukar S.,Khanwelkar, Rahul R.
, p. 7787 - 7792 (2007/10/03)
Novel routes for the synthesis of spiro derivatives of Meldrum's acid and 2-substituted malonic acid derivatives have been developed. Meldrum's acid was monoalkylated using a Michael addition reaction. Mono-Michael adducts were then alkylated using substituted haloalkanes, which on condensation gave spiro derivatives of Meldrum's acid. Bis Michael addition of Meldrum's acid with 1,5-diaryl-1,4-pentadien-3-one gave directly a spiro derivative of Meldrum's acid. These compounds and bis alkylated Meldrum's acid derivatives, on acidic methanolysis gave 2-substituted malonic acids.
Design and pharmacological activity of phosphinic acid based NAALADase inhibitors
Jackson,Tays,Maclin,Ko,Li,Vitharana,Tsukamoto,Stoermer,Lu,Wozniak,Slusher
, p. 4170 - 4175 (2007/10/03)
A novel series of phosphinic acid based inhibitors of the neuropeptidase NAALADase are described in this work. This series of compounds is the most potent series of inhibitors of the enzyme described to date. In addition, we have shown that these compounds are protective in animal models of neurodegeneration. Compound 34 significantly prevented neurodegeneration in a middle cerebral artery occlusion model of cerebral ischemia. In addition, in the chronic constrictive model of neuropathic pain, compound 34 significantly attenuated the hypersensitivity observed with saline-treated animals. These data suggest that NAALADase inhibition may provide a new approach for the treatment of both neurodegenerative disorders and peripheral neuropathies.
Influence of ring size on the outcome of sulfide contraction reactions with thiolactams. Isolation of bicyclic ketene S,N-acetals and thioisomuenchnones
Michael, Joseph P.,De Koning, Charles B.,Van der Westhuyzen, Christiaan W.,Fernandes, Manuel A.
, p. 2055 - 2062 (2007/10/03)
Reaction between diethyl bromomalonate and 3-phenylpyrrolidine-2-thione yielded a vinylogous urethane by the Eschenmoser sulfide contraction. However, with 3-substituted piperidine-2-thiones, sulfur was retained in the products, and a range of bicyclic heterocycles, including bicyclic ketene S,N-acetals (2-alkylidene-1,3-thiazolidin-4-ones) and stable thioisomuechnones, was isolated. A novel dimeric ketene S,N-acetal was characterised by X-ray crystallography.
