197314-92-4Relevant academic research and scientific papers
Structural features defining nf-κb inhibition by lignan-inspired benzofurans and benzothiophenes
Dao-Huy, Toan,Latkolik, Simone,Br?uer, Julia,Pfeil, Andreas,Stuppner, Hermann,Schnürch, Michael,Dirsch, Verena M.,Mihovilovic, Marko D.
, p. 1 - 20 (2020/08/07)
A series of 2-arylbenzofurans and 2-arylbenzothiophenes was synthesized carrying three different side chains in position five. The synthesized compounds were tested for NF-κB inhibition to establish a structure activity relationship. It was found that both, the side chain in position five and the substitution pattern of the aryl moiety in position two have a significant influence on the inhibitory activity.
Asymmetric Allylic C-H Alkylation via Palladium(II)/ cis-ArSOX Catalysis
Liu, Wei,Ali, Siraj Z.,Ammann, Stephen E.,White, M. Christina
supporting information, p. 10658 - 10662 (2018/09/06)
We report the development of Pd(II)/cis-aryl sulfoxide-oxazoline (cis-ArSOX) catalysts for asymmetric C-H alkylation of terminal olefins with a variety of synthetically versatile nucleophiles. The modular, tunable, and oxidatively stable ArSOX scaffold is key to the unprecedented broad scope and high enantioselectivity (37 examples, avg. > 90% ee). Pd(II)/cis-ArSOX is unique in its ability to effect high reactivity and catalyst-controlled diastereoselectivity on the alkylation of aliphatic olefins. We anticipate that this new chiral ligand class will find use in other transition metal catalyzed processes that operate under oxidative conditions.
Synthesis of fused furans by gas-phase pyrolysis of 2-allyloxyaryl-propenoic esters
Black, Michael,Cadogan,McNab, Hamish,MacPherson, Andrew D.,Roddam, V. Peter,Smith, Carol,Swenson, Helen R.
, p. 2483 - 2493 (2007/10/03)
Flash vacuum pyrolysis of 2-allyloxypropenoic esters (e.g. 7) gives benzo[b]furans (e.g. 32) in synthetically useful yields by sequential generation of a phenoxyl radical, cyclisation and ejection of the carboxylic ester function as a free radical leaving group. The method is compatible with a range of substituents on either the benzene ring or the propenoate chain, and is particularly effective for 2-substituted benzo[b]furans. The natural products 5-methoxybenzo[b]furan 1 and angelicin 2 have been synthesised in three and four steps respectively from commercially available starting materials by this route. Related cyclisations to give naphtho[2,1-b]furan 40 were complicated by competitive formation of naphtho[2,1-b]pyran-3-ones (e.g. 41 and 42), but the yield of the required product could be optimised by the choice of the radical precursor. Annelation of a furan ring onto a thlophene is also possible by this method, but lower yields are obtained in such pyrolyses.
