67838-02-2Relevant articles and documents
Iodoarene-Catalyzed Oxyamination of Unactivated Alkenes to Synthesize 5-Imino-2-Tetrahydrofuranyl Methanamine Derivatives
Deng, Xiao-Jun,Liu, Hui-Xia,Zhang, Lu-Wen,Zhang, Guan-Yu,Yu, Zhi-Xiang,He, Wei
, p. 235 - 253 (2021/01/09)
Reported here is the room-temperature metal-free iodoarene-catalyzed oxyamination of unactivated alkenes. In this process, the alkenes are difunctionalized by the oxygen atom of the amide group and the nitrogen in an exogenous HNTs2 molecule. This mild and open-air reaction provided an efficient synthesis to N-bistosyl-substituted 5-imino-2-tetrahydrofuranyl methanamine derivatives, which are important motifs in drug development and biological studies. Mechanistic study based on experiments and density functional theory calculations showed that this transformation proceeds via activation of the substrate alkene by an in situ generated cationic iodonium(III) intermediate, which is subsequently attacked by an oxygen atom (instead of nitrogen) of amides to form a five-membered ring intermediate. Finally, this intermediate undergoes an SN2 reaction by NTs2 as the nucleophile to give the oxygen and nitrogen difunctionalized 5-imino-2-tetrahydrofuranyl methanamine product. An asymmetric variant of the present alkene oxyamination using chiral iodoarenes as catalysts also gave promising results for some of the substrates.
mCPBA-mediated dioxygenation of unactivated alkenes for the synthesis of 5-imino-2-tetrahydrofuranyl methanol derivatives
Deng, Xiaojun,Zhang, Luwen,Liu, Huixia,Bai, Yu,He, Wei
supporting information, (2020/11/24)
A mCPBA-mediated, metal-free, intramolecular dioxygenation reaction of unactivated alkenes is reported. In the presence of m-chlorobenzoic peracid, different unsaturated amide substrates could be cyclized via epoxide intermediates, producing the corresponding 5-imino-2-tetrahydrofuranyl methanol products in up to 94% yield at room temperature.
Rhodium-Catalyzed Cyclization of O,ω-Unsaturated Alkoxyamines: Formation of Oxygen-Containing Heterocycles
Escudero, Julien,Bellosta, Véronique,Cossy, Janine
supporting information, p. 574 - 578 (2018/02/21)
O,ω-Unsaturated N-tosyl alkoxyamines undergo unexpected RhIII-catalyzed intramolecular cyclization by oxyamination to produce oxygen-containing heterocycles. Mechanistic studies show that an aziridine intermediate seems to be responsible for the formation of the heterocycles, possibly via a RhV species.
Photoredox-Catalyzed Intramolecular Aminodifluoromethylation of Unactivated Alkenes
Zhang, Zuxiao,Tang, Xiaojun,Thomoson, Charles S.,Dolbier, William R.
supporting information, p. 3528 - 3531 (2015/07/28)
A photoredox catalyzed aminodifluoromethylation of unactivated alkenes has been developed in which HCF2SO2Cl is used as the HCF2 radical source. Sulfonamides were active nucleophiles in the final step of a tandem addition/oxidation/cyclization process to form pyrrolidines, and esters were found to cyclize to form lactones. Thus, a variety of pyrrolidines and lactones were obtained in moderate to excellent yield. In order for the cyclization reactions to be efficient, a combination of a copper catalyst (Cu(dap)2Cl) and silver carbonate was crucial to suppressing a competing chloro, difluoroalkylation process.
Intramolecular Hydroalkoxylation of Unactivated Alkenes Using Silane-Iodine Catalytic System
Fujita, Shoji,Abe, Masanori,Shibuya, Masatoshi,Yamamoto, Yoshihiko
supporting information, p. 3822 - 3825 (2015/08/18)
A novel catalytic system using I2 and PhSiH3 for the intramolecular hydroalkoxylation of unactivated alkenes is described. NMR study indicated that in situ generated PhSiH2I is a possible active catalytic species. This catalytic system allows an efficient intramolecular hydroalkoxylation of phenyl-, trialkyl-, and 1,1-dialkyl-substituted alkenes as well as a variety of unactivated monoalkyl- and 1,2-dialkyl-substituted alkenes at room temperature. Mechanistic consideration based on significant experimental observations is also discussed.
Discovery of a novel melanin concentrating hormone receptor 1 (MCHR1) antagonist with reduced hERG inhibition
Mihalic, Jeffrey T.,Fan, Pingchen,Chen, Xi,Chen, Xiaoqi,Fu, Ying,Motani, Alykhan,Liang, Lingming,Lindstrom, Michelle,Tang, Liang,Chen, Jin-Long,Jaen, Juan,Dai, Kang,Li, Leping
scheme or table, p. 3781 - 3785 (2012/07/27)
An initial SAR study resulted in the identification of the novel, potent MCHR1 antagonist 2. After further profiling, compound 2 was discovered to be a potent inhibitor of the hERG potassium channel, which prevented its further development. Additional opt
SUBSTITUTED PHENYL CYCLOALKYL PYRROLIDINE (PIPERIDINE) SPIROLACTAMS AND AMIDES, PREPARATION AND THERAPEUTIC USE THEREOF
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Page/Page column 37-38, (2011/12/02)
The present invention discloses and claims respectively a series of substituted phenyl cycloalkyl pyrrolidine (piperidine) spirolactams and amides of formula (I) (Ia) and formula (Ib) as described herein. More specifically, the compounds of this invention
SUBSTITUTED N-HETEROARYL SPIROLACTAM BIPYRROLIDINES, PREPARATION AND THERAPEUTIC USE THEREOF
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Page/Page column 29, (2011/12/02)
The present invention discloses and claims a series of substituted N-heteroaryl spirolactam bipyrrolidines of formula ( Wherein R1, R2, Q1, Q2, Q3, Q4, X, m, n, p and s are as described her
SUBSTITUTED N-PHENYL SPIROLACTAM BIPYRROLIDINES, PREPARATION AND THERAPEUTIC USE THEREOF
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Page/Page column 23, (2011/12/02)
The present invention discloses and claims a series of substituted N-phenyl spirolactam bipyrrolidines of formula (I). (Formula (I)) Wherein R1, R2, R3, R4, m, n, p and s are as described herein. More specifical
Copper-catalysed intramolecular O-H addition to unactivated alkenes
Adrio, Luis A.,Quek, Louisa Shuyi,Taylor, Jason G.,Kuok (Mimi) Hii, King
supporting information; experimental part, p. 10334 - 10338 (2010/02/28)
Intramolecular cyclisation of ω-alkenoic acids and alkenols can be achieved using a catalytic amount of Cu(OTf)2 to afford lactones and cyclic ethers, offering a practical alternative to existing catalysts.