24807-15-6Relevant academic research and scientific papers
Au(I)-Catalyzed Hydration of 1-Iodoalkynes Leading to α-Iodoketones
Cazin, Catherine S. J.,Gómez-Herrera, Alberto,Hashim, Ishfaq Ibni,Nahra, Fady,Porré, Marre
, p. 6790 - 6794 (2020/11/23)
A catalytic protocol for the Au(I)-catalyzed hydration of 1-iodoalkynes is disclosed. The use of Au(I)–NHC catalyst enabled the straightforward synthesis of a variety of α-iodomethyl ketones in good to excellent yields. The utility of this simple method is further highlighted by showcasing iodination/hydration and hydration/oxidation sequential protocols leading to the construction of molecular complexity.
α-Carbonylimine to α-Carbonylamide: An efficient oxidative amidation approach
Padala, Anil K.,Mupparapu, Nagaraju,Singh, Deepika,Vishwakarma, Ram A.,Ahmed, Qazi Naveed
supporting information, p. 3577 - 3586 (2015/06/08)
Abstract Our interest in generating amide bonds by employing the activated C=N system has led to the development of an efficient oxidative amidation reaction between 2-oxoaldehyde and weak nucleophilic amines (anilines, benzamides and sulfonamides). Mechanistic studies support the involvement of α-carbonylimine (-CO-C=N-) based compounds or intermediates as a central feature of the reaction, in which an adjacent CO moiety enhances the electrophilicity of the C=N system, which favors attack of the oxidant (TBHP or SeO2), thereby resulting in the generation of the desired products in good yields. The direct oxidative coupling of 2-oxoaldehydes and weak nucleophilic amines has been accomplished through either MgSO4-TBHP-pyridine/CuBr, or SeO2·pyridine promoted methods. In the current study, SeO2·pyridine emerged as a versatile reagent with which to promote initial α-carbonylimine formation between 2-oxoaldehyde and weak nucleophilic amine, and subsequent oxidation to the corresponding α-carbonylamide. The reported methodology constitutes one of the few reports of the synthesis of α-ketoamides from anilines, perhaps the second report for the generation of α-ketoimides, and the first report of the generation of 2-oxoamides with sulfonamides.
TBHP/TEMPO-mediated oxidative synthesis of imides from amides
Yu, Hui,Chen, Yuegang,Zhang, Yonghao
, p. 531 - 534 (2015/05/27)
A new protocol for the synthesis of imides has been developed. In the presence of copper catalyst, N-benzylamides were oxidized to the corresponding imides by TBHP/TEMPO system in moderate to good yields. Imides were synthesized through the oxidation of N-benzylamides by TBHP/TEMPO system in moderate to good yields.
The oxidative cross-coupling of benzonitriles with multiform substrates: A domino strategy inspired easy access to α-keto-imides
Kalmode, Hanuman P.,Vadagaonkar, Kamlesh S.,Chaskar, Atul C.
, p. 429 - 438 (2015/02/19)
An iodine-promoted highly efficient convergent synthesis of α-ketoimides from multiform substrates and benzonitriles through oxidative imidation reaction is described. This domino oxidative imidation process involves cleavage of C-H bond and construction of C-O and C-N bonds. This method could be a powerful compliment to the existing methods owing to its use of abundantly available starting materials and reagents.
Metal-free in situ sp3, sp2, and sp C-H functionalization and oxidative cross coupling with benzamidines hydrochloride: A promising approach for the synthesis of α-ketoimides
Kalmode, Hanuman P.,Vadagaonkar, Kamlesh S.,Chaskar, Atul C.
, p. 60316 - 60326 (2015/02/19)
A new metal-free tandem protocol for the synthesis of α-ketoimides via sp3, sp2, and sp C-H functionalization followed by oxidative cross coupling with benzamidines hydrochloride using catalytic iodine with TBHP in DMSO has been developed. A wide range of functional group tolerance, an inexpensive catalyst, operational simplicity and good to excellent yields of the products are the striking features of this method.
I2-catalyzed oxidative cross-coupling of methyl ketones and benzamidines hydrochloride: A facile access to α-ketoimides
Wu, Xia,Gao, Qinghe,Liu, Shan,Wu, Anxin
, p. 2888 - 2891 (2014/06/23)
An iodine-catalyzed oxidative cross-coupling of C-H/N-H has been demonstrated. This simple and efficient approach constructed α-ketoimides in good to excellent yields from methyl ketones and benzamidines hydrochloride under metal-free and peroxide-free co
Oxidative decarboxylation of 4-arylmethylidene-5(4H)-oxazolones using cerium(IV) ammonium nitrate
Ram, S. Raja,Devi, A. Rama,Iyengar, D. S.
, p. 718 - 719 (2007/10/03)
Oxidative decarboxylation of azlactones by cerium(IV) ammonium nitrate yields 2-arylglyoxyamide in very good yields.
Photo-oxygenation of N-Unsubstituted Pyrazin-2-ones and Alkoxypyrazines
Nishio, Takehiko,Kondo, Masaji,Omote, Yoshimori
, p. 2497 - 2500 (2007/10/02)
Dye-sensitized photo-oxgenation of N-unsubstituted pyrazin-2-ones (1b-d) afforded the endoperoxides (2b-d) in 61-72percent yield.On being heated the endoperoxides (2) decomposed to give the unsymmetrical imides (4) accompanied by a loss of benzonitrile. 2
