68471-55-6Relevant academic research and scientific papers
Direct Synthesis of Enamides via Electrophilic Activation of Amides
Berger, Martin,Kaiser, Daniel,Maulide, Nuno,Spie?, Philipp
, p. 10524 - 10529 (2021/07/28)
A novel, one-step N-dehydrogenation of amides to enamides is reported. This reaction employs the unlikely combination of LiHMDS and triflic anhydride, which serves as both the electrophilic activator and the oxidant, and is characterized by its simple setup and broad substrate scope. The synthetic utility of the formed enamides was readily demonstrated in a range of downstream transformations.
Chiral multi-substituted 4 - hydroxy chroman compound and its preparation method and application
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Paragraph 0051; 0053, (2017/07/01)
The invention discloses a chiral polysubstituted 4-hydroxychroman compound, and a preparation method and application thereof. The compound has a general structural formula as shown in a formula I which is described in the specification. The preparation method comprises a step of subjecting a salicylaldehyde compound as shown in a general structural formula II and a tertiary alkenyl amide as shown in a general structural formula III to an intermolecular nucleophilic tandem reaction in the presence of a chiral Lewis acid catalyst so as to realize high-efficiency high-selectivity preparation of the chiral polysubstituted 4-hydroxychroman compound. According to the method, the raw material alkenyl amide which can be easily prepared on large scale and the cheap and easily available chiral catalyst are used, and the novel chiral polysubstituted 4-hydroxychroman bicyclo derivative product which cannot be synthesized by using other methods is prepared under mild reaction conditions; and the produce has a stable structure, high yield and enantioselectivity and good application prospects and can be easily separated and purified.
Visible-light, metal-free α-amino C(sp3)-H activation through 1,5-hydrogen migration: A concise method for the preparation of bis(indolyl)alkanes
Shaaban, Saad,Roller, Alexander,Maulide, Nuno
, p. 7643 - 7647 (2015/12/31)
A photoredox catalytic, metal-free method for C-H functionalization α to amines directly leads to the formation of bis(indolyl)alkane products in good to excellent yields. This transformation hinges on a smooth 1,5-hydrogen migration to an aryl radical in
Ring contraction of of α,β-unsaturated cyclic amines with cis-dihydroxylation at the α,β-position
Libendi, Samuel S.,Demizu, Yosuke,Matsumura, Yoshihiro,Onomura, Osamu
experimental part, p. 311 - 321 (2009/09/06)
α,β-Unsaturated cyclic amines are oxidized by OsO4 to afford α,β-cis-dihydroxylated compounds which are thermodynamically transformed into ring-opened keto-alcohols. The keto-alcohols are then cyclized to form synthetically useful ring-contracted cyclic amines.
Synthesis of polycyclic lactams and sultams by a cascade ring-closure metathesis/isomerization and subsequent radical cyclization
Bressy, Cyril,Menant, Christine,Piva, Olivier
, p. 577 - 582 (2007/10/03)
Starting from readily available substrates, a new one-pot procedure has been devised to prepare polycyclic lactams and sultams. 2-Pyrrolines obtained from N,N-bisallylamides by ring-closure metathesis and subsequent isomerization promoted by ruthenium hyd
On a facile synthesis of melatonin and other related indoles
Marais, Wilhelmina,Holzapfel, Cedric W.
, p. 3681 - 3691 (2007/10/03)
An efficient laboratory synthesis for melatonin and other related indoles utilising enamides and enecarbamates is described.
A Convenient Route to β-Aryl-substituted Cyclic Enamines as Key Synthetic Intermediates of Sceletium and Amaryllidaceae Alkaloids
Matsumura, Yoshihiro,Terauchi, Jun,Yamamoto, Takashi,Konno, Takashi,Shono, Tatsuya
, p. 8503 - 8512 (2007/10/02)
Aryl groups were introduced into the position β to the nitrogen atom of cyclic amines by carrying out the anodic α-methoxylation of cyclic amine derivatives, the elimination of methanol from the oxidized products, the halomethoxylation of the resulting α,β-unsaturated cyclic amine derivatives, the replacement of the α-methoxy group with an aryl group, and the silver ion-promoted migration of the α-aryl group to the β-position, consecutively.This method was applied to the synthesis of some alkaloids such as (+/-)-mesembrine.
