42768-87-6Relevant articles and documents
Oxidation of Nonactivated Anilines to Generate N-Aryl Nitrenoids
Deng, Tianning,Mazumdar, Wrickban,Ford, Russell L.,Jana, Navendu,Izar, Ragda,Wink, Donald J.,Driver, Tom G.
supporting information, p. 4456 - 4463 (2020/03/05)
A low-temperature, protecting-group-free oxidation of 2-substituted anilines has been developed to generate an electrophilic N-aryl nitrenoid intermediate that can engage in C-NAr bond formation to construct functionalized N-heterocycles. The exposure of 2-substituted anilines to PIFA and trifluoroacetic acid or 10 mol percent Sc(OTf)3 triggers nitrenoid formation, followed by productive and selective C-NAr and C-C bond formation to yield spirocyclic- or bicyclic 3H-indoles or benzazepinones. Our experiments demonstrate the breadth of these oxidative processes, uncover underlying fundamental elements that control selectivity, and demonstrate how the distinct reactivity patterns embedded in N-aryl nitrenoid reactive intermediates can enable access to functionalized 3H-indoles or benzazepinones.
Chemo- and Regioselective Asymmetric Friedel-Crafts Reaction of Furans and Thiophenes with α,β-Unsaturated Aldehydes through Dual Activation
Zhang, Xiao-Ru,Zhou, Su-Lan,Yuan, Yi,Du, Wei,Chen, Ying-Chun
supporting information, p. 1771 - 1774 (2017/09/30)
A highly chemo- and regioselective Friedel-Crafts alkylation reaction of furans and thiophenes has been developed, which relies on the activation from the remote conjugated Mukaiyama silyl enol ether motif. Excellent enantioslectivity is generally obtained in reactions with α,β-unsaturated aldehydes under the well-established iminium ion catalysis of a chiral secondary amine.
NOUVELLE METHODE DE SYNTHESE DES (FURYL-2)-2 CYCLANONES
Duval, O.,Gomes, L. Mavoungou
, p. 4471 - 4476 (2007/10/02)
A high yield new synthesis of 2-(2-furyl)-cycloalkanones is described.The first step consists in a condensation of 2,5-dimethoxy-2,5-dihydro-furan with various cyclic β-ketoesters in acidic medium.The decarboalkoxylation is then realised in the presence o