127459-01-2Relevant articles and documents
A simple and effective synthesis of benzolactones and benzolactams by noncatalytic benzylic oxidation of cyclic benzylic ethers and N-protected cyclic benzylic amines with sodium chlorite as an oxidant
Song, Ai-Ru,Yu, Jun,Zhang, Chi
, p. 2903 - 2909 (2012)
Sodium chlorite (NaClO was shown to be capable of oxidizing cyclic benzylic ethers and N-protected cyclic benzylic amines in a heterogeneous solvent system of 1,1,1-trichloroethane and water at 55-65°C to give synthetically useful benzolactones and benzolactams, respectively, in high-to-excellent yields. Georg Thieme Verlag Stuttgart ? New York.
Radical oxidation of amides and related compounds with hypervalent tert- butylperoxyiodanes: Synthesis of imides and tert-butylperoxyamide acetals
Ochiai, Masahito,Kajishima, Daisuke,Sueda, Takuya
, p. 5541 - 5544 (1999)
tert-Butylperoxyiodane undergoes oxidation of the methylene groups α to the nitrogen atom of amides (or carbamates) yielding imides or tert- butylperoxyamide acetals, depending on the reaction conditions. A proposed mechanism involves generation of carbon-centered radicals α to the nitrogen atom.
Synthesis and applications of a new epoxy-isoindolinone synthesis and applications of a new epoxy-isoindolinone
Chou, Shang-Shing P.,Hsu, Sung-Lin
, p. 726 - 737 (2015)
A new epoxy-isoindolinone was stereoselectively synthesized, and its reactions gave several interesting products including a new 6-azabicyclo[3.2.1]octane derivative.
Rhodium-catalyzed intramolecular aminocarbonylation of aryl halides using aldehydes as a source of carbon monoxide
Morimoto, Tsumoru,Fujioka, Masahiko,Fuji, Koji,Tsutsumi, Ken,Kakiuchi, Kiyomi
, p. 154 - 155 (2003)
The reaction of N-Ts-(2-bromophenyl)alkylamines with aldehydes in the presence of a catalytic amount of a rhodium complex results in the intramolecular aminocarbonylation of the aryl halides to give five-, six-, and seven-membered benzolactams.
A New Aerobic Oxidation System Using Pd-Cu Catalysts in the Presence of CO
Miyamoto, Masanori,Minami, Yumiko,Ukaji, Yutaka,Kinoshita, Hideki,Inomata, Katsuhiko
, p. 1149 - 1152 (1994)
Oxidation of benzylic ethers, tosylamides, and 9,10-dihydroanthracene could be performed efficiently under O2 and CO atmosphere in the presence of PdCl2-CuCl2 catalysts to give the corresponding esters (lactones), amides and anthraquinone, respectively.
Merging C-H Activation and Strain-Release in Ruthenium-Catalyzed Isoindolinone Synthesis
Hu, Xiao-Qiang,Liu, Zi-Kui,Hou, Ye-Xing,Xu, Ji-Hang,Gao, Yang
supporting information, p. 6332 - 6336 (2021/08/23)
The merger of strain-release of 1,2-oxazetidines with carboxylic acid directed C-H activation in catalytic synthesis of isoindolinones is reported for the first time. This reaction opens a new and sustainable avenue to prepare a range of structurally dive
Br?nsted Acid Catalyzed Dearomatization by Intramolecular Hydroalkoxylation/Claisen Rearrangement: Diastereo- and Enantioselective Synthesis of Spirolactams
Chen, Peng-Fei,Wang, Binju,Wu, Peng,Ye, Long-Wu,Zhou, Bo
, p. 27164 - 27170 (2021/11/22)
Described herein is a novel Br?nsted acid catalyzed intramolecular hydroalkoxylation/Claisen rearrangement, allowing the practical and atom-economic synthesis of a range of valuable spirolactams from readily available ynamides in generally good to excellent yields with excellent diastereoselectivities and broad substrate scope. Importantly, an unexpected dearomatization of nonactivated arenes and heteroaromatic compounds is involved in this tandem sequence. Moreover, an asymmetric version of this tandem cyclization was also achieved by efficient kinetic resolution by chiral phosphoric acid catalysis. In addition, the [3,3]-rearrangement is shown to be kinetically preferred over the related [1,3]-rearrangement by theoretical calculations.
Autotandem Catalysis: Inexpensive and Green Access to Functionalized Ketones by Intermolecular Iron-Catalyzed Amidoalkynylation/Hydration Cascade Reaction via N-Acyliminium Ion Chemistry
Abdallahi, Sidi Mohamed,Ewies, Ewies F.,El-Shazly, Mohamed,Ould Elemine, Brahim,Hadou, Abderrahmane,Moncol, Ján,Lawson, Ata Martin,Daich, Adam,Othman, Mohamed
supporting information, p. 15440 - 15449 (2021/10/07)
Iron-based catalysts were applied in cascade-type reactions for the synthesis of different carbonyl compounds. The reactions proceeded by a new iron-catalyzed cascade of alkynylation/hydration by using both the σ- and π-Lewis acid properties of iron salts. The alkynylation reactions of several endo and exocyclic acetoxylactams were achieved with three different catalysts including FeCl3 ? 6H2O, FeCl3, and Fe(OTf)3 showing the efficiency of σ-Lewis acidity of iron (III) salts in catalyzing the alkynylation reaction. We also demonstrated that the reaction sequence could be shortened by the direct use of hydroxylactams, leading to an environmentally friendly protocol, avoiding the need to perform unnecessary lengthy steps. A combination of the hard/soft iron Lewis acid properties was then used to implement an unprecedented tandem intermolecular alkynylation/intramolecular hydration sequence allowing expedient access to a new carbonyl structures from trivial materials.
Ynamide Smiles Rearrangement Triggered by Visible-Light-Mediated Regioselective Ketyl-Ynamide Coupling: Rapid Access to Functionalized Indoles and Isoquinolines
Chen, Yang-Bo,Sun, Zhou,Wang, Ze-Shu,Ye, Long-Wu,Zhang, Hao-Wen,Zhu, Chunyin
, p. 3636 - 3644 (2020/03/06)
In the past decades, significant advances have been made on radical Smiles rearrangement. However, the eventually formed radical intermediates in these reactions are limited to the amidyl radical, except for the few examples initiated by a N-centered radical. Here, a novel and practical radical Smiles rearrangement triggered by photoredox-catalyzed regioselective ketyl-ynamide coupling is reported, which represents the first radical Smiles rearrangement of ynamides. This method enables facile access to a variety of valuable 2-benzhydrylindoles with broad substrate scope in generally good yields under mild reaction conditions. In addition, this chemistry can also be extended to the divergent synthesis of versatile 3-benzhydrylisoquinolines through a similar ketyl-ynamide coupling and radical Smiles rearrangement, followed by dehydrogenative oxidation. Moreover, such an ynamide Smiles rearrangement initiated by intermolecular photoredox catalysis via addition of external radical sources is also achieved. By control experiments, the reaction was shown to proceed via key ketyl radical and α-imino carbon radical intermediates.
Biomimetic aerobic oxidation of amino alcohols to lactams
Babu, Beneesh P.,Endo, Yoshinori,Baeckvall, Jan-E.
supporting information, p. 11524 - 11527,4 (2012/12/11)
The right path: N-Protected amino alcohols undergo aerobic and biomimetic oxidation to the corresponding lactams in the presence of a ruthenium catalyst and a combination of electron-transfer mediators under air (see scheme). The reaction was used for the synthesis of five-, six-, and seven-, membered lactams and showed good tolerance to a number of N-protecting groups. Copyright
