32119-53-2Relevant articles and documents
Stevens rearrangement of anilinium salts by the action sodium carbonate hexahydrate
Shakhbazyan,Babakhanyan,Grigoryan,Kocharyan
, p. 1608 - 1610 (2003)
Anilinium salts containing an allyl-like group together with various functionally substituted receiving groups undergo Stevens rearrangement by the action of sodium carbonate hexahydrate in the absence of a solvent. As a result, both N-methylaniline deriv
Iron-catalyzed reductive strecker reaction
Yan, Fachao,Huang, Zijun,Du, Chen-Xia,Bai, Jian-Fei,Li, Yuehui
, p. 188 - 194 (2021/02/03)
Strecker reaction is widely applied for the synthesis of amino acids from aldehydes, amines and cyanides. Herein, we report the FeI2-catalyzed reductive Strecker type reaction of formamides instead of aldehydes to produce amino acetonitriles. The challenging capture of carbinolamine intermediates by CN? was achieved via Fe catalysis. This approach afforded better yields than the use of Ir- or Rh-catalysts. The application ability of this methodology is demonstrated by 1) one-pot construction of (13C labeled) complex molecules from CO2 via amino acetonitrile intermediates and 2) convenient production of homologated carboxylic acids from aldehydes.
Metal-Free α-C(sp3)-H Aroylation of Amines via a Photoredox Catalytic Radical-Radical Cross-Coupling Process
Xu, Guo-Qiang,Xiao, Teng-Fei,Feng, Guo-Xuan,Liu, Chen,Zhang, Baoxin,Xu, Peng-Fei
supporting information, p. 2846 - 2852 (2021/05/05)
Here we describe an unprecedented metal-free C(sp3)-H aroylation of amines via visible-light photoredox catalysis, which provides a straightforward route for the construction of a useful α-amino aryl ketone skeleton. Additionally, a number of selected products exhibit good biological activity for protecting PC12 cell damage, which shows that this skeleton has the potential to become a new neuroprotective agent. Finally, a series of mechanism experiments indicate that this transformation undergoes a photoredox catalytic radical-radical cross-coupling pathway.
Metal and Oxidant Free Construction of Substituted- and/or Polycyclic Indoles: A Useful Alternative to Bischler and Related Syntheses
De Crescentini, Lucia,Favi, Gianfranco,Mantellini, Fabio,Mari, Giacomo,Santeusanio, Stefania
supporting information, (2020/08/27)
A wide range of substituted indoles or polycyclic derivatives containing the indole core are easily accessible by acidic treatment of aromatic amines and 1,2-diaza-1,3-dienes. Unlike the related indole-Bischler synthesis, the regioselectivity of the method here reported is unique and predictable, the yields are generally good and also electron withdrawing substituted indoles are smoothly recovered.
Solvent-Free Synthesis of α-Amino Ketones from α-Hydroxyl Ketones via A Novel Tandem Reaction Sequence Based on Heyns Rearrangement
Li, Ling-Yu,Zeng, Qing-Le,Li, Guang-Xun,Tang, Zhuo
supporting information, p. 694 - 699 (2019/03/26)
Heyns rearrangement have been famous for carbohydrate chemists for several decades. However, this reaction was underrated as a useful method for synthetic chemists due to preparative shortcomings. Herein we developed an efficient method for the synthesis of pharmaceutically important α-amino ketones from readily available α-hydroxy ketones and secondary amines through a tandem reaction sequence based on Heyns rearrangement. The reaction smoothly proceeded by using catalytic PTSA as catalyst without solvent. Primary and secondary α-hydroxy ketones were readily used and regioselectively afforded the correspondingly α-amino ketones with moderate yield.
Overcoming solid handling issues in continuous flow substitution reactions through ionic liquid formation
Kashani, Saeed,Sullivan, Ryan J.,Andersen, Mads,Newman, Stephen G.
supporting information, p. 1748 - 1753 (2018/04/30)
Substitutions such as acylations, arylations, and alkylations are some of the most commonly run reactions for building complex molecules. However, the requirement of a stoichiometric base to scavange acid by-products creates significant challenges when operating in continuous flow due to solid handling issues associated with precipitating base·HX salts. We present a general and simple strategy to overcome these solid handling issues through the use of acid scavenging organic bases that generate low- to moderate-melting ionic liquids upon protonation. The application of these bases towards the most commonly run substitutions are demonstrated, enabling reactions to be run in flow without requiring additional equipment, specific solvents, or dilute reaction conditions to prevent clogging.
N-Bromosuccinimide promoted and base switchable one pot synthesis of α-imido and α-amino ketones from styrenes
Shinde, Mahesh H.,Kshirsagar, Umesh A.
supporting information, p. 858 - 861 (2016/01/15)
An N-Bromosuccinimide (NBS) promoted one pot strategy for the synthesis of α-amino functionalized aryl ketones starting from commercially available styrenes has been developed. NBS participates in multiple tasks, such as bromonium ion formation, oxidation of bromohydrin and providing a nucleophilic nitrogen source. The reaction can easily be switched between α-imido and α-amino ketones by the choice of base. This one pot strategy was successfully applied for the synthesis of psychoactive drug candidates, amfepramone, mephedrone and 4-MEC.
A photoredox catalyzed radical-radical coupling reaction: Facile access to multi-substituted nitrogen heterocycles
Li, Weipeng,Duan, Yingqian,Zhang, Muliang,Cheng, Jian,Zhu, Chengjian
supporting information, p. 7596 - 7599 (2016/07/06)
Visible light induced photoredox catalysis is an efficient method for radical activation. Herein, we report the photoredox catalysis involving an intramolecular radical-radical coupling reaction that proceeds through a biradical intermediate. This protocol represents a new synthetic route to construct multi-substituted N-heterocycles. Four, five and six-membered N-heterocyclic structures with a quaternary carbon center are accessible under mild conditions.
Iron-catalyzed direct α-arylation of α-amino carbonyl compounds with indoles
Zhang, Yan,Ni, Minjie,Feng, Bainian
supporting information, p. 1550 - 1554 (2016/02/10)
A mild and general α-arylation of α-amino carbonyls with indoles catalyzed by Fe(ClO4)3 has been developed. C-H activation is smoothly fulfilled by using TBHP as the oxidant with good yields. Two hydrogen dissociations make this transformation more environmentally benign because of high atom efficiency.
Reductive cyclization of halo-ketones to form 3-hydroxy-2-oxindoles via palladium catalyzed hydrogenation: a hydrogen-mediated Grignard addition
Shin, Inji,Ramgren, Stephen D.,Krische, Michael J.
supporting information, p. 5776 - 5780 (2015/08/03)
Abstract The reductive cyclization of N-oxoacyl ortho-bromoanilides to form 3-hydroxy-2-oxindoles under the conditions of palladium catalyzed hydrogenation is described. This work may be viewed as a prelude to intermolecular hydrogen-mediated Grignard-typ
