271-58-9Relevant academic research and scientific papers
A laser flash photolysis study on 2-azido-N,N-diethylbenzylamine - The reactivity of iminoquinone methides in solution
Bucher, Goetz
, p. 2463 - 2475 (2001)
Photolysis of 2-azido-N,N-diethylbenzylamine (1) in acetonitrile solution in the presence of various quenchers yields products of common nitrene chemistry (that is, derived from a didehydroazepine or a triplet nitrene), together with products arising from trapping of stereoisomeric iminoquinone methides. These intermediates are formed in a monophotonic process, by dediazotation of the precursor combined with a 1,4-hydrogen shift. The reactivity of the iminoquinone methides (IQM) towards a variety of quenchers, including dienophiles and various nucleophiles, has been explored, using acetonitrile, DMF, and n-hexane as solvents. IQM reacts efficiently with electron deficient dienophiles [kq(maleic anhydride) = 2.4·107 M-1 s-1], but not with simple olefins such as cyclohexene. IQM shows low to medium reactivity towards simple primary or secondary amines [kq(n-propylamine) = 6.4·104 M-1 s-1], medium reactivity with sterically unhindered simple alcohols [kq(methanol) = 4.6·106 M-1 s-1], and high to very high reactivity towards thiols [kq(n-dodecanethiol) = 1.1·109 M-1 s-1], diols, and triols [kq(glycerol) = 1.5·108 M-1 s-1], and sugars [kq(D-glucose) = 1.0·109 M-1 s-1]. IQM also reacts rapidly with cytosine: kq(cytosine) = 3.4·108 M-1 s-1, while the reaction with adenine or thymine is less efficient [kq(adenine) = 6.4·107 M-1 s-1, kq(thymine) = 7.7·106 M-1 s-1].
The Elimination of Masses 27 and 28 from the + Ion of 2-Nitrotoluene
Herbert, C. G.,Larka, E. A.,Beynon, J. H.
, p. 306 - 310 (1984)
The expulsion of neutral fragments of masses 27 and 28 from metastable + ions derived from 2-nitrotoluene has been observed.The relative abundances of the resulting fragment ions, together with the kinetic energy released in each process, has been compared with similar fragmentations of + ions derived from other precursor molecules.In this way, the nature of the neutral fragments and the structure of the + ions from 2-nitrotoluene has been investigated.The most likely structure is the 1,2-benzisoxazolenium cation although the coexistence of other structures cannot be ruled out on the present evidence.
Metal-Free [3+2] Annulation of Ynamides with Anthranils to Construct 2-Aminoindoles
Zhang, Jingyi,Li, Ying,Zhang, Chaofeng,Wang, Xiao-Na,Chang, Junbiao
supporting information, p. 2029 - 2035 (2021/04/05)
A novel metal-free [3+2] annulation of ynamides with anthranils provides a facile, flexible, environmentally friendly, and atom-economical route to 2-aminoindoles. This synthetic process proceeds with efficiency, excellent regioselectivity, and wide functional group tolerance under mild conditions. Moreover, the obtained 2-aminoindole products represent a multifunctional platform for the construction of various 2-aminoindolyl frameworks.
Palladium-catalyzed carbonylative cyclization of benzyl chlorides with anthranils for the synthesis of 3-arylquinolin-2(1: H)-ones
Liu, Jian-Li,Xu, Ren-Rui,Wang, Wei,Qi, Xinxin,Wu, Xiao-Feng
supporting information, p. 3584 - 3588 (2021/05/04)
An efficient carbonylative procedure for the synthesis of 3-arylquinoin-2(1H)-ones has been established. Through a palladium-catalyzed aminocarbonylation of benzyl chlorides with anthranils, a variety of 3-arylquinoin-2(1H)-one products were obtained in moderate to excellent yields with good functional group tolerance. This journal is
I2-DMSO mediated oxidative amidation of methyl ketones with anthranils for the synthesis of: α -ketoamides
Zhuang, Shi-Yi,Tang, Yong-Xing,Chen, Xiang-Long,Wu, Yan-Dong,Wu, An-Xin
supporting information, p. 4258 - 4262 (2021/05/31)
An I2-DMSO mediated oxidative amidation of methyl ketones using anthranils as masked N-nucleophiles has been developed for the direct synthesis of α-ketoamides with high atom-economy. This metal-free process involves reductive N-O bond cleavage of anthranils and oxidative C-N bond formation of methyl ketones under mild conditions. The iodo group and electrophilic formyl group provide multiple possibilities for further functionalization of α-ketoamides.
Access to acridones by tandem copper(i)-catalyzed electrophilic amination/Ag(i)-mediated oxidative annulation of anthranils with arylboronic acids
Huang, Yan-Xia,Huang, Zhuo-Jun,Jiang, Chun-Yong,Liang, Jing-Yi,Liang, Qiu-Ping,Shu, Bing,Xie, Hui,Zeng, Jun-Yi,Zhang, Shang-Shi,Zhou, Binhua
supporting information, p. 8487 - 8491 (2021/10/20)
An efficient and practical approach for the synthesis of medicinally important acridones was developed from anthranils and commercially available arylboronic acids by a tandem copper(i)-catalyzed electrophilic amination/Ag(i)-mediated oxidative annulation strategy. This new and straightforward protocol displayed a broad substrate scope (25 examples) and high functional group tolerance. What's more, a possible mechanistic proposal was also presented.
Metal-Free Synthesis of Anthranils by PhIO Mediated Heterocyclization of ortho-Carbonyl Anilines
Garia, Alankrita,Grover, Jatin,Jain, Nidhi
, p. 4125 - 4131 (2021/08/24)
Here, we report a metal-free synthesis of anthranils from ortho-carbonyl anilines using PhIO as a sole additive under ambient conditions. This methodology did not require any external additives and delivered anthranils in excellent yields with broad substrate scope. The mechanistic studies suggest that the reaction proceeds via in-situ generation of iminoiodane leading to nitrene and a subsequent nucleophilic attack from oxygen of ortho-carbonyl aniline on nitrene results in heterocyclization.
Ambient reductive synthesis of N-heterocyclic compounds over cellulose-derived carbon supported Pt nanocatalyst under H2atmosphere
Wu, Yunyan,Wu, Yunyan,Zhao, Yanfei,Zhao, Yanfei,Wang, Huan,Wang, Huan,Zhang, Fengtao,Zhang, Fengtao,Li, Ruipeng,Li, Ruipeng,Xiang, Junfeng,Wang, Zhenpeng,Han, Buxing,Liu, Zhimin
, p. 3820 - 3826 (2020/07/06)
N-heterocyclic compounds are important chemicals, and their reductive synthesis using H2 under mild conditions is attractive but challenging. Herein, we report chemoselective hydrogenation of 2-nitroacylbenzenes to 2,1-benzisoxazoles under ambient conditions for the first time, wihch is achieved over cellulose-derived carbon (c-C) supported Pt nanocatalyst (Pt/c-C), and a series of 2,1-benzisoxazoles can be obtained in excellent yields. Pt/c-C also shows high performance for ambient reductive amination of levulinic acid with H2, accessing various pyrrolidones in excellent yields. The systematic studies indicated that the c-C support played multiple roles in catalysis with enhancing electron density of the Pt nanoparticles and activating reactant molecules. Especially, the O-containing groups on the c-C surface provided the c-C support with both acid and base features, thus endowing Pt/c-C with high performances. This work provides an accessible and highly efficient catalyst for reductive synthesis of N-heterocycles using H2 under ambient conditions, which may have promising applications.
Copper-Catalyzed Annulation or Homocoupling of Sulfoxonium Ylides: Synthesis of 2,3-Diaroylquinolines or α,α,β-Tricarbonyl Sulfoxonium Ylides
Zhu, Shuai,Shi, Kai,Zhu, Hao,Jia, Zhe-Kang,Xia, Xiao-Feng,Wang, Dawei,Zou, Liang-Hua
supporting information, p. 1504 - 1509 (2020/03/03)
An unprecedented copper-catalyzed reaction of sulfoxonium ylides and anthranils is reported that enables an easy access to 2,3-diaroylquinolines through a [4+1+1] annulation. Copper-catalyzed homocoupling of sulfoxonium ylides provided α,α,β-tricarbonyl sulfoxonium ylides, which provides a strategy to extend the carbon chain through C-C bond formation. The utility of the products as well as the mechanistic details of the process are presented.
Gold-Catalyzed Intermolecular Formal [4 + 2 + 2]-Cycloaddition of Anthranils with Allenamides
Wang, Cheng,Xu, Guangyang,Shao, Ying,Tang, Shengbiao,Sun, Jiangtao
supporting information, p. 5990 - 5994 (2020/08/12)
The construction of eight-membered rings is a challenging issue due to unfavorable transannular strain and entropic barriers. We report herein a gold-catalyzed formal [4 + 2 + 2] cycloaddition reaction of anthranils with allenamides to deliver oxa-bridged eight-membered heterocycles in accepted yields with unique E/Z configuration. Moreover, the asymmetric [4 + 2 + 2] cycloaddition by using chiral phosphoramidite gold catalyst has also been conducted.
