81462-47-7Relevant academic research and scientific papers
Generation of Donor/Donor Copper Carbenes through Copper-Catalyzed Diyne Cyclization: Enantioselective and Divergent Synthesis of Chiral Polycyclic Pyrroles
Hong, Feng-Lin,Wang, Ze-Shu,Wei, Dong-Dong,Zhai, Tong-Yi,Deng, Guo-Cheng,Lu, Xin,Liu, Rai-Shung,Ye, Long-Wu
, p. 16961 - 16970 (2019/10/16)
The generation of metal carbenes from readily available alkynes represents a significant advance in metal carbene chemistry. However, most of these transformations are based on the use of noble-metal catalysts and successful examples of such an asymmetric version are still very scarce. Here a copper-catalyzed enantioselective cascade cyclization of N-propargyl ynamides is reported, enabling the practical and atom-economical construction of diverse chiral polycyclic pyrroles in generally good to excellent yields with wide substrate scope and excellent enantioselectivities (up to 97:3 e.r.). Importantly, this protocol represents the first copper-catalyzed asymmetric diyne cyclization. Moreover, mechanistic studies revealed that the generation of donor/donor copper carbenes is presumably involved in this 1,5-diyne cyclization, which is distinctively different from the related gold catalysis, and thus it constitutes a novel way for the generation of donor/donor metal carbenes.
De Novo Synthesis of Phenols and Naphthols through Oxidative Cycloaromatization of Dienynes
Rong, Ming-Guang,Qin, Tian-Zhu,Liu, Xin-Rui,Wang, Hong-Fa,Zi, Weiwei
supporting information, p. 6289 - 6293 (2018/10/09)
In this work, a rhodium-catalyzed oxidative cycloaromatization of dienynes, which provides a highly straightforward and efficient way to access polysubstituted naphthols and phenols under mild conditions, is described. Challenged electron-withdrawing groups are well tolerated in this protocol, and late-stage phenyl ring formation is demonstrated.
1,2,3-Triazoles as inhibitors of indoleamine 2,3-dioxygenase 2 (IDO2)
R?hrig, Ute F.,Majjigapu, Somi Reddy,Caldelari, Daniela,Dilek, Nahzli,Reichenbach, Patrick,Ascencao, Kelly,Irving, Melita,Coukos, George,Vogel, Pierre,Zoete, Vincent,Michielin, Olivier
, p. 4330 - 4333 (2016/08/18)
Indoleamine 2,3-dioxygenase 2 (IDO2) is a potential therapeutic target for the treatment of diseases that involve immune escape such as cancer. In contrast to IDO1, only a very limited number of inhibitors have been described for IDO2 due to inherent diff
Photochemistry of chloro-2-vinylstilbenes
Brouw, P. M. op den,Laarhoven, W. H.
, p. 58 - 67 (2007/10/02)
Short irradiation at 300 nm of α-chloro- and β-chloro-2-vinylstilbene (20 and 21) leads to a mixture of 2-vinyltolane (35) and 2-vinylstilbene (1) accompanied by the cis- and trans-isomers of the starting compounds.Evidence is found for the occurrence of an ionic intermediate during the photolysis of 20 in methanol.At 360 nm, an additional, small amount of 1-chloro-endo- and 1-chloro-exo-6-phenylbenzobicyclohex-2-ene (39) is formed formed from 20.The elimination of hydrogen chloride also occurs during the irradiation of 2-(2-chlorovinyl)stilbene (23) and leads to 2-ethynylstilbene (41).The acetylenic compounds are photocyclized into 2-phenylnaphthalene (38).However, 2-(1-chlorovinyl)stilbene (22) reacts without loss of chlorine to give 1-chloro-exo-5-phenylbenzobicyclo-hex-2-ene (40).This exceptional reaction mode is due to a much higher rate of photocyclization resulting from less distortion in the stilbene moiety and a preference for a conformation better suited to the reaction of the 2-(1-chlorovinyl)stilbene molecule.It is shown that both isomers of 22 can photocyclize into 40.
The Photochemistry of 2-Vinyldiphenylacetylene and Related Compounds
Brouw, Paul M. op den,Laarhoven, Wim H.
, p. 795 - 800 (2007/10/02)
Irradiation of solutions of 2-vinyldiphenylacetylene (5) under anaerobic conditions gives 2-phenylnaphtalene (9) in 90 percent yield.Several derivatives of (5) behave similarly.The reaction is ascribed to the primary formation of a cyclic allene (29), as has been proposed previously for the analogous photocyclization of 1,4-diarylbutenynes into phenylaromatic compounds.The end-product arises from (29) either via a 1,5-hydrogen shift or by addition and elimination of a proton.Irradiation of 2-ethynylstilbene (21) also yields (9), but 1-ethynylphenanthrene (22) is formed as a side-product.
