1700-88-5Relevant academic research and scientific papers
Potassium Iodide-Promoted One-Pot Synthesis of Fluoroalkylated Quinoxalines via a Tandem Michael Addition/Azidation/Cycloamination Approach
Wu, Jun,Zhang, Hui,Ding, Xiao,Tan, Xuefei,Chen, Jie,He, Weimin,Deng, Hongmei,Song, Liping,Shen, Hong C.,Cao, Weiguo
, p. 9422 - 9429 (2018)
Fluoroalkylated quinoxlines with various groups were efficiently synthesized via a one-pot tandem Michael addition/azidation/cycloamination process. Under the mild and metal-free conditions, a bis-imine intermediate (4a) was detected and isolated for the
2,4-Bis(fluoroalkyl)quinoline-3-carboxylates as Tools for the Development of Potential Agrochemical Ingredients
Aribi, Fallia,Panossian, Armen,Vors, Jean-Pierre,Pazenok, Sergii,Leroux, Frédéric R.
, p. 3792 - 3802 (2018)
Based on an easy and scalable method for the synthesis of quinoline derivatives substituted by fluorinated groups at both the C-2 and C-4 positions developed in our laboratory, we have devised an approach to the synthesis of a new series of unprecedented 2,4-bis(fluoroalkyl)quinoline-3-carboxylates in just two steps. After standard saponification, the latter gave the corresponding 2,4-bis(fluoroalkyl)quinoline-3-carboxylic acids, which served as pivotal intermediates for post-functionalization reactions. Indeed, the carboxylic group could then be derivatized according to known procedures to introduce chemical diversity at the C-3 position of these unprecedented structures. The resulting highly functionalized quinolines can serve as a platform for the development of biologically active molecules with strong potential for agrochemical research.
Chemoselective Nitrosylation of Anilines and Alkynes via Fragmentary or Complete NO Incorporation
Pan, Jun,Li, Xinyao,Lin, Fengguirong,Liu, Jianzhong,Jiao, Ning
supporting information, p. 1427 - 1442 (2018/04/20)
The cycloaddition reactions have been explored extensively and provided an efficient strategy for the synthesis of cyclic compounds. Traditionally, the reaction partners were in extenso incorporated into the cyclic products without fragmentation. From a different perspective, if certain fragmentations via chemical-bond cleavage are involved in this cycloaddition reaction, it would change the assembly sequence and enable more product diversity. Here, we report a chemoselective nitrosylation of anilines and alkynes through fragmentary or complete NO radical incorporation. The formation of multiple C–N bonds, an unexpected C–N bond, and N=O bond cleavage make this fragmentary cycloaddition reaction an efficient approach to 2,5-dihydrooxazoles, 1H-1,2,3-triazole 2-oxides or quinoxaline N-oxides. Facile operation in open-air, metal-free, and mild conditions renders this protocol particularly practical and attractive. A series of mechanistic studies and density functional theory calculations were also conducted, which help to explain the fragmentary or complete NO incorporation processes, broadening the field of new reaction discovery. Exploring novel structures and developing convenient and direct methods to achieve them are an essential issue in synthetic chemistry. In traditional cycloaddition reactions, the reaction partners are in extenso incorporated into the cyclic compound products. In contrast, the fragmentary incorporation of the reaction partners via chemical-bond cleavage in cycloaddition reactions would change the assembly sequence and enable more product diversity. However, fragmentary incorporation in cycloaddition reactions remains a challenging issue because of the high bond-dissociation energy and poor selectivity. This paper reports a fragmentary cycloaddition reaction that enables a series of new structures through a controllable radical process. This work also reveals the diversity of transformation of free radical intermediates. The accessible products might also trigger some interest in pharmaceutical science and materials science. Cycloaddition reactions provide an efficient strategy for the synthesis of cyclic compounds and have been well developed. However, cycloaddition reactions with fragmentary partner incorporation via the cleavage of multiple bonds, which allows for more structural diversity than traditional cycloaddition reactions, have seldom been reported. Here, we describe a chemoselective nitrosylation of anilines and alkynes through fragmentary or complete NO radical incorporation for an efficient approach to 2,5-dihydrooxazoles, 1H-1,2,3-triazole 2-oxides, or quinoxaline N-oxides.
Hypervalent iodine(III)-promoted: N -incorporation into N -aryl vinylogous carbamates to quinoxaline diesters: Access to 1,4,5,8-tetraazaphenanthrene
Sagar,Vidaycharan, Shinde,Shinde, Anand H.,Sharada, Duddu S.
supporting information, p. 4018 - 4022 (2016/06/14)
A novel oxidative N-incorporation strategy for synthesis of quinoxaline diesters under metal-free conditions is described for the first time. The mild reaction conditions allow for this transformation via the formation of two C(sp2)-N bonds utilizing cheaply available NaN3 as the N-atom source. N-Aryl vinylogous carbamates in this study undergo azidation at enamino C(sp2)-H selectively. The robustness of this strategy is further demonstrated by the synthesis of a valuable 1,4,5,8-tetraazaphenanthrene derivative using a mild and convenient approach.
Reductive amination/cyclization of ω-trifluoromethyl keto esters to trifluoromethylated δ-amino alcohols and lactams
Wan, Wen,Hou, Jie,Jiang, Haizhen,Yuan, Zongqian,Goubin, Ma.,Zhao, Gang,Hao, Jian
experimental part, p. 1778 - 1786 (2010/06/15)
A reductive amination/cyclization approach towards biologically interesting trifluoromethylated four- to seven-membered ring lactams from simply prepared ω-trifluoromethyl keto esters in good to excellent yields has been developed. In addition, trifluorom
