22020-69-5Relevant academic research and scientific papers
Synthesis of Nitrogen-Containing Heterocycles through Catalytic Dehydrative Cyclization Reactions
Rodriguez Del Rey, Freddy O.,Floreancig, Paul E.
supporting information, p. 150 - 154 (2021/01/09)
Re2O7 in hexafluoroisopropyl alcohol provides access to cationic intermediates from alcohols through the intermediacy of perrhenate esters. This manuscript describes the application of the system to the formation of a number of weakly basic heterocyclic systems through dehydration reactions and intramolecular nucleophilic addition. The influence of the substrate structure on the reaction rates and stereocontrol is discussed with respect to intermediate ion pairs.
Visible light bromide catalysis for oxazoline, pyrrolidine, and dihydrooxazine synthesesviaCsp3-H functionalizations
Kaur, Navdeep,Ziegelmeyer, Elizabeth C.,Farinde, Olutayo N.,Truong, Jonathon T.,Huynh, Michelle M.,Li, Wei
supporting information, p. 10387 - 10390 (2021/10/14)
A catalytic benzylic Csp3-H functionalization protocol is described here. This visible light-mediated process is centered on the utilization of a bromide catalyst and oxidant to generate a nitrogen (N)-centered radical for a site-selective hydrogen atom transfer (HAT) process. This strategy enabled the unconventional syntheses of a number of N-heterocycles dependent on the amide identity. We also discovered a nucleophilicity-dependent kinetic resolution for stereochemical differentiation of Csp3-H bonds that enabled the stereoselective synthesis ofcis- andtrans-oxazolines.
RuV-Acylimido Intermediate in [RuIV(Por)Cl2]-Catalyzed C–N Bond Formation: Spectroscopic Characterization, Reactivity, and Catalytic Reactions
Che, Chi-Ming,Hong, Dan-Yan,Huang, Jie-Sheng,Law, Siu-Man,Liu, Yungen,Lo, Vanessa Kar-Yan,Toy, Patrick H.,Wu, Liangliang
supporting information, p. 18619 - 18629 (2021/06/09)
Metal-catalyzed C?N bond formation reactions via acylnitrene transfer have recently attracted much attention, but direct detection of the proposed acylnitrenoid/acylimido M(NCOR) (R=aryl or alkyl) species in these reactions poses a formidable challenge. H
Use of Hypervalent Iodine in the Synthesis of Isomeric Dihydrooxazoles
Carlucci, Claudia,Tota, Arianna,Colella, Marco,Ronamazzi, Giuseppe,Clarkson, Guy J.,Luisi, Renzo,Degennaro, Leonardo
, p. 428 - 436 (2018/06/11)
[Figure not available: see fulltext.] A convenient synthesis of 2- and/or 3-oxazolines has been developed depending on the structure and stereochemistry of the starting amino alcohol. PhI(OAc)2 acted as oxidant on the intermediate imine, as sup
Visible-Light-Promoted Metal-Free Aerobic Hydroxyazidation of Alkenes
Yang, Bo,Lu, Zhan
, p. 8362 - 8365 (2017/12/08)
A highly efficient visible-light-promoted metal-free aerobic hydroxyazidation of alkenes has been developed. This protocol was operationally simple with broad substrate scope using relatively simple and readily available starting materials, such as alkene
METHOD FOR PRODUCING OXAZOLE COMPOUND
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Paragraph 0049;0053-0054, (2016/10/10)
PROBLEM TO BE SOLVED: To provide a method for producing an oxazole compound which makes it possible to obtain an oxazole compound inexpensively and safely. SOLUTION: A ketone compound, a nitrile compound, an iodinating agent, an oxidizing agent and an acid catalyst are mixed for a reaction to obtain an oxazole compound. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2016,JPOandINPIT
Mn-Catalyzed Highly Efficient Aerobic Oxidative Hydroxyazidation of Olefins: A Direct Approach to β-Azido Alcohols
Sun, Xiang,Li, Xinyao,Song, Song,Zhu, Yuchao,Liang, Yu-Feng,Jiao, Ning
supporting information, p. 6059 - 6066 (2015/05/27)
(Chemical Equation Presented). An efficient Mn-catalyzed aerobic oxidative hydroxyazidation of olefins for synthesis of β-azido alcohols has been developed. The aerobic oxidative generation of azido radical employing air as the terminal oxidant is disclosed as the key process for this transformation. The reaction is appreciated by its broad substrate scope, inexpensive Mn-catalyst, high efficiency, easy operation under air, and mild conditions at room temperature. This chemistry provides a novel approach to high value-added β-azido alcohols, which are useful precursors of aziridines, β-amino alcohols, and other important N- and O-containing heterocyclic compounds. This chemistry also provides an unexpected approach to azido substituted cyclic peroxy alcohol esters. A DFT calculation indicates that Mn catalyst plays key dual roles as an efficient catalyst for the generation of azido radical and a stabilizer for peroxyl radical intermediate. Further calculation reasonably explains the proposed mechanism for the control of C-C bond cleavage or for the formation of β-azido alcohols.
A facile preparation of various N-heterocycles using amides and olefins
Gratia, Synthia S.,Vigneau, Edward S.,Eltayeb, Sumiea,Patel, Kishan,Meyerhoefer, Terence J.,Kershaw, Sonia,Huang, Victor,De Castro, Michael
, p. 448 - 452 (2014/01/06)
We herein report a one pot approach for the synthesis of various nitrogen containing heterocycles including: oxazolines, thiazolines, and dihydro dioxazines via the addition of amides to olefins in the presence of N-iodosuccinimide (NIS) and propionitrile
"On water": Efficient iron-catalyzed cycloaddition of aziridines with heterocumulenes
Sengoden, Mani,Punniyamurthy, Tharmalingam
supporting information, p. 572 - 575 (2013/02/23)
In suspension: The reaction of aziridines with heterocumulenes in the presence of Fe(NO3)3×9 H2O in aqueous suspension provides access to functionalized five-membered heterocycles in good to high yields. This protocol has a wide substrate scope, is simple, and uses a nontoxic and cheap catalyst. Copyright
Synthesis of 2,5-disubstituted oxazoles and oxazolines catalyzed by ruthenium(II) porphyrin and simple copper salts
Zhong, Chuan Long,Tang, Bo Yang,Yin, Ping,Chen, Yue,He, Ling
scheme or table, p. 4271 - 4277 (2012/06/18)
A novel and moderate synthesis of 2,5-disubstituted oxazoles and oxazolines involving ruthenium(II) porphyrin-copper chloride catalyzed cyclization was developed. These reactions using readily available benzene carboxylic acids and phenylethenes or phenylacetylenes are performed under mild conditions. The reactions proceed in series, giving rise to the formation of an intermolecular C-N bond and an intramolecular C-O bond, which yield oxazole or oxazoline derivatives simultaneously.
