10001-54-4Relevant academic research and scientific papers
Redox Cyclization of Amides and Sulfonamides with Nitrous Oxide for Direct Synthesis of Heterocycles
Lai, Zhencheng,Wang, Chaorong,Li, Jiaming,Cui, Sunliang
, p. 2017 - 2021 (2020)
Herein we report a redox cyclization of amides and sulfonamides with nitrous oxide (N2O) for the direct synthesis of heterocycles. Various amides and sulfonamides could undergo directed ortho metalation (DoM) by treatment with BuLi, and the lithium intermediate could be trapped by N2O gas to achieve redox cyclization. N2O serves as a N-atom donor to mediate the intramolecular coupling of lithium species toward heterocycle formation with free external oxidant. This protocol offers a direct synthesis of heterocycles with features of readily available starting materials, simple operation, and a broad substrate scope.
Towards a Sequential One-Pot Preparation of 1,2,3-Benzotriazin-4(3H)-ones Employing a Key Cp*Co(III)-catalyzed C?H Amidation Step
Chirila, Paula G.,Skibinski, Lauren,Miller, Keith,Hamilton, Alex,Whiteoak, Christopher J.
supporting information, p. 2324 - 2332 (2018/04/30)
1,2,3-benzotriazin-4(3H)-one derivatives have been recognised for their potential application as pesticides and pharmaceuticals and new methodologies for their preparation, starting from readily accessible reagents would therefore be an attractive proposition. A wide range of differently substituted benzamides are readily available, which provide an excellent substrate scaffold for the application of direct C?H functionalization protocols. In this context, herein we report the use of a Cp*Co(III) catalyst for the amidation of these benzamides, using 1,4,2-dioxazol-5-ones as amidating agent. The isolable intermediate 2-acetamido benzamide products can thereafter be converted to the desired 1,2,3-benzotriazin-4(3H)-one derivatives through the use of tert-butyl nitrite under mild conditions. It was found to be possible to perform the second step with the crude reaction mixture obtained from the initial C?H amidation step, leading to the overall development of a facile one-pot procedure for the preparation of a range of substituted 1,2,3-benzotriazin-4(3H)-one derivatives, requiring only 5 hours of reaction time, which is also applicable on a gram scale. In addition, the key Cp*Co(III)-catalyzed C?H amidation step has been studied by DFT calculations in order to fully elucidate the mechanism. (Figure presented.).
Mild and efficient TBAI-catalyzed synthesis of 1,2,3-benzotriazine-4-(3H)-ones from tert-butyl nitrite and 2-aminobenzamides under acid-free conditions
Yan, Yizhe,Li, Hongyi,Niu, Bin,Zhu, Changrui,Chen, Ting,Liu, Yanqi
supporting information, p. 4170 - 4173 (2016/08/24)
A facile and efficient annulation of 2-aminobenzamides and tert-butyl nitrite was developed, affording 1,2,3-benzotriazine-4-(3H)-ones in good yields under mild conditions. Notably, the reaction was carried out in the absence of strong acid and tert-butyl
Potassium Iodide/tert-Butyl Hydroperoxide-Mediated Oxidative Annulation for the Selective Synthesis of N-Substituted 1,2,3-Benzotriazine-4(3H)-ones Using Nitromethane as the Nitrogen Synthon
Yan, Yizhe,Niu, Bin,Xu, Kun,Yu, Jianhua,Zhi, Huanhuan,Liu, Yanqi
supporting information, p. 212 - 217 (2016/02/14)
A novel and efficient oxidative annulation of 2-aminobenzamides with nitromethane has been developed for the chemoselective synthesis of N-substituted 1,2,3-benzotriazine-4(3H)-ones in moderate to excellent yields under transition metal-free conditions. T
Preparation method of N-substituted 1,2,3-phentriazine-4-ketone
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Paragraph 0066; 0067; 0068, (2016/10/08)
The invention discloses a preparation method of N-substituted 1,2,3-phentriazine-4-ketone. The preparation method specifically comprises the following step: by taking anthranilamide as a reaction substrate, taking tert-butyl nitrite as a nitrogen source a
