808114-08-1Relevant academic research and scientific papers
"on Water" Promoted Ullmann-Type C-N Bond-Forming Reactions: Application to Carbazole Alkaloids by Selective N-Arylation of Aminophenols
Chakraborti, Gargi,Paladhi, Sushovan,Mandal, Tirtha,Dash, Jyotirmayee
, p. 7347 - 7359 (2018/07/29)
The Ullmann-type cross coupling of a variety of aromatic, aliphatic amines with aryl halides is reported using a CuI-based catalytic system in combination with an easily accessible prolinamide ligand in aqueous media. The method is mild and tolerant to air, moisture, and a wide range of functional groups, providing a novel way to access a variety of aminated products. Secondary amines like heteroaromatic amines and nucleobases have also been used, affording the corresponding coupling products in good to excellent yields. Moreover, this method has been employed for chemoselective C-N arylation of aminophenols and further utilized for the synthesis of carbazole natural products, avoiding the protection and deprotection steps.
Copper-catalyzed N=H insertion and oxidative aromatization cascade: Facile synthesis of 2-arylaminophenols
Ding, Dong,Lv, Xiaobing,Li, Jian,Xu, Guangyang,Ma, Bing,Sun, Jiangtao
, p. 1539 - 1542 (2014/06/09)
A copper-catalyzed cascade reaction of N-H insertion and oxidative aromatization has been developed. 2-Arylaminophenols have been prepared in moderate to high yields from the diazo substrates. Moreover, this newly established methodology allows efficient access to natural 1-oxygenated carbazole alkaloids, such as glycozolicine and murrayafoline A. Copper falls: A copper-catalyzed cascade reaction of N=H insertion and oxidative aromatization yields 2-arylaminophenols. This newly established methodology also allows efficient access to natural 1-oxygenated carbazole alkaloids, such as glycozolicine and murrayafoline A.
A Pd-catalyzed cascade reaction of N-H insertion and oxidative dehydrogenative aromatization: A new entry to 2-amino-phenols
Ding, Dong,Lv, Xiaobing,Li, Jian,Qiu, Lin,Xu, Guangyang,Sun, Jiangtao
, p. 4084 - 4088 (2014/06/10)
A palladium-catalyzed cascade reaction of N-H insertion (NHI) and oxidative dehydrogenative aromatization (ODA) has been developed, which affords a straightforward and efficient way to access the carbazole precursors (2-arylamino-phenols) as well as to prepare 2-alkylamino-phenols from non-aromatic substrates. This journal is the Partner Organisations 2014.
Direct amination of phenols under metal-free conditions
Yu, Jianzhong,Wang, Yongtao,Zhang, Peizhi,Wu, Jun
supporting information, p. 1448 - 1454 (2013/07/26)
Herein, we disclose the metal-free synthesis of arylamines via the direct amination of phenols using aminating reagents. This reaction procedure uses easy accessible aminating reagents and provides a versatile synthetic route to a broad range of arylamines with various functionalities in good to excellent yield. By using a two-step route of amination and oxidative coupling reaction, we synthesized three naturally occurring carbazole alkaloids: murrayafoline A, mukonine, and clausenine from two commercially available phenols. Georg Thieme Verlag Stuttgart · New York.
Acid-free synthesis of carbazoles and carbazolequinones by intramolecular Pd-catalyzed, microwave-assisted oxidative biaryl coupling reactions efficient syntheses of murrayafoline A, 2-methoxy-3-methylcarbazole, and glycozolidine
Sridharan, Vellaisamy,Antonia Martin,Carlos Menendez
supporting information; experimental part, p. 4614 - 4621 (2009/12/05)
A mild and. efficient methodology for the synthesis of oxygenated. carbazoles from diarylamines under non-acidic conditions was developed, based on a palladium-catalyzed, microwave-assisted double C-H bond activation process. This new protocol was successfully applied to the synthesis of three naturally occurring carbazoles, namely murrayafoline A, 2-methoxy-3-methylcarbazole, and glycozolidine. The scope of the reaction was also expanded, to include the synthesis of benzo fused carbazolequinones. Wiley-VCH Verlag GmbH & Co. KGaA.
Synthesis of oxygenated carbazoles by palladium-mediated oxidative double C-H activation of diarylamines assisted by microwave irradiation
Sridharan, Vellaisamy,Martín, Ma. Antonia,Menéndez, J. Carlos
, p. 2375 - 2378 (2008/02/09)
Microwave irradiation in the presence of palladium acetate and traces of dimethylformamide allows the fast and efficient cyclodehydrogenation of diphenylamines into carbazoles. The scope of the microwave-assisted reaction is broader than that of the one using conventional conditions in that it allows the preparation of oxygenated carbazoles without apparent loss in yield. The applicability of the method to the preparation of carbazole alkaloids has been demonstrated by the development of a total synthesis of murrayafoline A, which proceeds in 50% overall yield from commercially available materials and is the shortest and most efficient route for the preparation of this alkaloid to date. Georg Thieme Verlag Stuttgart.
Total synthesis of the natural carbazoles Murrayanine and Murrayafoline A, based on the regioselective Diels-Alder addition of exo-2-oxazolidinone dienes
Benavides, Adriana,Peralta, Javier,Delgado, Francisco,Tamariz, Joaquin
, p. 2499 - 2504 (2007/10/03)
A new synthesis of the natural carbazoles Murrayanine (1) and Murrayafoline A (3) is described. The key step in the synthetic route involved the regioselective cycloaddition of the diene 4,5-dimethylene-3-phenyl-1,3- oxazolidin-2-one (4) to acrolein (6) c
