2009-97-4Relevant academic research and scientific papers
A new method for the synthesis of N-protected β-amino-α-keto esters from fluoroalkanesulfonylazides and α-keto esters
Zhu, Shizheng,Jin, Guifang,Xu, Yong
, p. 4389 - 4394 (2003)
In the presence of a secondary amine, treatment of α-keto esters with fluoroalkanesulfonyl azides at room temperature afforded N-sulfonyl protected β-amino-α-keto esters in good to excellent yields. This reaction provided a novel, direct and convenient access to N-sulfonyl protected β-amino-α-keto esters from α-keto esters and fluoroalkanesulfonyl azides under mild conditions. However, the reaction of fluoroalkanesulfonyl azides with β-ketoester enamines afforded two products: N-fluoroalkanesulfonyl amidines and diazoacetate. The reaction mechanism is discussed.
Solvent-Directed Click Reaction between Active Methylene Compounds and Azido-1,3,5-triazines
Yan, Ziqiang,Li, Yuanheng,Ma, Mingming
, p. 7204 - 7208 (2019)
A novel solvent-directed click reaction between active methylene compounds and azido-1,3,5-triazines has been developed. In aqueous solution, the regiospecific trisubstituted 1,2,3-triazole products are quickly synthesized in high yields under mild conditions and easy to separate without column chromatography. This click reaction is controlled by the protonation of a nitrogen anion intermediate, and the postulated mechanism is substantiated by DFT calculations.
Development of a povarov reaction/carbene generation sequence for alkenyldiazocarbonyl compounds
Jadhav, Appaso Mahadev,Pagar, Vinayak Vishnu,Liu, Rai-Shung
, p. 11809 - 11813 (2012)
Rings aplenty: A HOTf-catalyzed (Tf=trifluoromethanesulfonyl) Povarov reaction of alkenyldiazo species has been developed and delivers diazo-containing cycloadducts stereoselectively (see scheme). The resulting cycloadducts provide access to six- and seven-membered azacycles through the generation of metal carbenes as well as the functionalization of diazo group. Copyright
Efficient solid/liquid phase-transfer catalytic diazo transfer synthesis
Jaszay, Zsuzsa M.,Pham, Truong Son,Goenczi, Katalin,Petnehazy, Imre,Toke, Laszlo
, p. 1574 - 1579 (2010)
A simple and efficient solid/liquid phase-transfer catalytic diazo transfer reaction for the synthesis of diazocarbonyl, diazophosphonyl, and diazophosphinyl compounds is reported. Copyright
Rh(III)-catalyzed chelation-assisted intermolecular carbenoid functionalization of α-imino Csp3-H bonds
Chen, Xun,Xie, Ying,Xiao, Xinsheng,Li, Guoqiang,Deng, Yuanfu,Jiang, Huanfeng,Zeng, Wei
, p. 15328 - 15331 (2015)
A Rh(iii)-catalyzed cross-coupling/cyclization cascade of α-imino Csp3-H bonds with donor/acceptor α-acyl diazocarbonyl compounds has been developed. This novel transformation involves ligand-directed Csp3-H bond functionalization with carbenoids under the pyridine-chelation assistance, and offered an efficient access to synthetically versatile polysubstituted N-(2-pyridyl)pyrroles with a broad range of functional group tolerance.
A dual-protein cascade reaction for the regioselective synthesis of quinoxalines
Li, Fengxi,Li, Zhengqiang,Tang, Xuyong,Wang, Chunyu,Wang, Lei,Wang, Zhi,Xu, Yaning
, p. 3900 - 3904 (2020)
In this work, an efficient dual-protein (lipase and hemoglobin) system was successfully constructed for the regioselective synthesis of quinoxalines in water. A set of quinoxalines were obtained in high yields under optimal reaction conditions. This dual-protein method exhibited a regioselectivity higher than those of previously reported methods. This study not only provides a green and mild strategy for the synthesis of quinoxalines but also expands the application of lipase and hemoglobin in organic synthesis.
Azidotris(diethylamino)phosphonium bromide: A self-catalyzing diazo transfer reagent
McGuiness, Mark,Shechter, Harold
, p. 4987 - 4990 (1990)
Acidic methylene compounds are conveniently converted to diazo compounds in high yields by azidotris(diethylamino)phosphonium bromide, 1, in diethyl ether using only a catalytic amount of base. The product diazo compounds are easily separated from the co-product hexaethylphosphorimidic triamide hydrobromide.
Transition metal-free steric controlled one-pot synthesis of highly substituted N-amino 1,2,3-triazole derivatives via diazo transfer reaction from β-keto esters
Nagarajan, Rajendran,Jayashankaran, Jayadevan,Emmanuvel, Lourdusamy
, p. 2612 - 2615 (2016)
An efficient, simple protocol for the one-pot synthesis of N-amino 1,2,3-triazole from β-keto esters has been described. This method involves diazo transfer reaction into in situ generated hydrazones using imidazole sulfonyl azide as the nitrogen source.
Rh-Catalyzed Coupling of Acrylic/Benzoic Acids with α-Diazocarbonyl Compounds: An Alternative Route for α-Pyrones and Isocoumarins
Hong, Chao,Liu, Zhanxiang,Yu, Shuling,Zhang, Yuhong
supporting information, p. 815 - 820 (2022/02/07)
A coupling of acrylic acids/benzoic acids with α-diazocarbonyl compounds has been realized by a combined catalytic system of rhodium catalyst and Zn(OAc)2 additive. The presence of Zn(OAc)2 obviously accelerates the C(sp2)
Enantioselective Synthesis of Nitrogen-Nitrogen Biaryl Atropisomers via Copper-Catalyzed Friedel-Crafts Alkylation Reaction
Guo, Chang-Qiu,Liu, Ren-Rong,Lu, Chuan-Jun,Wang, Xiao-Mei,Xu, Qi,Zhang, De-Bing,Zhang, Peng
supporting information, p. 15005 - 15010 (2021/09/30)
Nitrogen-nitrogen bonds containing motifs are ubiquitous in natural products and bioactive compounds. However, the atropisomerism arising from a restricted rotation around an N-N bond is largely overlooked. Here, we describe a method to access the first enantioselective synthesis of N-N biaryl atropisomers via a Cu-bisoxazoline-catalyzed Friedel-Crafts alkylation reaction. A wide range of axially chiral N-N bisazaheterocycle compounds were efficiently prepared in high yields with excellent enantioselectivities via desymmetrization and kinetic resolution. Heating experiments showed that the axially chiral bisazaheterocycle products have high rotational barriers.
