1071493-66-7Relevant articles and documents
Palladium-catalyzed double carbonylation-based diversity-oriented synthesis of 3,4-dihydroisoquinoline-1-carboxamides
Masui, Hisashi,Ishizawa, Natsumi,Fuse, Shinichiro,Takahashi, Takashi
, p. 6354 - 6360 (2015)
Abstract A novel palladium-catalyzed double carbonylation approach toward the synthesis of 3,4-dihydroisoquinoline-1-carboxamides is reported. The method developed involves an initial palladium-catalyzed double carbonylation of an N-protected alkylamine a
FUSED [1,2,4]THIADIAZINE DERIVATIVES WHICH ACT AS KAT INHIBITORS OF THE MYST FAMILY
-
, (2019/03/17)
A compound of formula (I): which inhibits the activity of one or more KATs of the MYST family, i.e., TIP60, KAT6B, MOZ, HBO1 and MOF.
Palladium-Catalyzed Domino Allenamide Carbopalladation/Direct C-H Allylation of Heteroarenes: Synthesis of Primprinine and Papaverine Analogues
Hédouin, Jonathan,Schneider, Cédric,Gillaizeau, Isabelle,Hoarau, Christophe
supporting information, p. 6027 - 6032 (2018/10/05)
Palladium-catalyzed intramolecular carbopalladation onto allenamides completed by direct C-H allylation of heterocycles is studied. The domino construction/heteroarylation of isoquinolone process is first achieved. A general three-step one-pot strategy, i
Synthesis of a potent aminopyridine-based nnos-inhibitor by two recent no-carrier-added 18f-labelling methods
Drerup, Christian,Ermert, Johannes,Coenen, Heinz H.
, (2016/09/23)
Nitric oxide (NO), an important multifunctional signaling molecule, is produced by three isoforms of NO-synthase (NOS) and has been associated with neurodegenerative disorders. Selective inhibitors of the subtypes iNOS (inducible) or nNOS (neuronal) are of great interest for decoding neurodestructive key factors, and 18F-labelled analogues would allow investigating the NOS-function by molecular imaging with positron emission tomography. Especially, the highly selective nNOS inhibitor 6-((3-((3-fluorophenethylamino)methyl)phenoxy)methyl)-4-methylpyridin-2-amine (10) lends itself as suitable compound to be 18F-labelled in no-carrier-added (n.c.a.) form. For preparation of the 18F-labelled nNOS-Inhibitor [18 F]10 a "build-up" radiosynthesis was developed based on a corresponding iodonium ylide as labelling precursor. The such activated phenethyl group of the compound was efficiently and regioselectively labelled with n.c.a. [18 F]fluoride in 79% radiochemical yield (RCY). After conversion by reductive amination and microwave assisted displacement of the protecting groups, the desired nNOS-inhibitor was obtained in about 15% total RCY. Alternatively,for a simplified "late-stage" 18F-labelling procedure a corresponding boronic ester precursor was synthesized and successfully used in a newer, copper(II) mediated n.c.a. 18F-fluoro-deboroniation reaction, achieving the same total RCY. Thus, both methods proved comparatively suited to provide the highly selective NOS-inhibitor [18 F]10 as probe for preclinical in vivo studies.
Approach to the synthesis of indoline derivatives from diaryliodonium salts
Landge, Kamalkishor P.,Jang, Keun Sam,Lee, Sang Yeul,Chi, Dae Yoon
, p. 5705 - 5713 (2012/09/07)
An effective method of constructing the indoline moiety via intramolecular nucleophilic ring closure of a diaryliodonium salt is described. Diacetoxyiodoarene compounds (1a-1e) were converted into intermediate Koser's reagent and coupled with arylstannanes (7-10) to form diaryliodonium salts (11a-14e). Indoline compounds with different N-protecting groups, 15, 16, 17, and 18, were synthesized in higher yields by treating salts (11a-14e) with Cs2CO3 and TEMPO. Regardless of the electronic environment of five para-substituted iodoarenes and the natures of four N-protected arylstannane groups, the conversion proceeded well to afford corresponding indolines in yields of 72-84 and 70-84%, respectively.
The endocyclic restriction test: The geometries of nucleophilic substitutions at sulfur(VI) and sulfur(II)
Jarboe, Stephen G.,Terrazas, Michael S.,Beak, Peter
supporting information; experimental part, p. 9627 - 9632 (2009/04/07)
(Chemical Equation Presented) The trajectories for nucleophilic substitutions at sulfur(VI) and sulfur(II) have been investigated by the endocyclic restriction test. On the basis of double-labeling experiments, the sulfur(VI) transfer in the conversion of 1 to 2 is found to be intramolecular, while the sulfur(VI) transfer in the conversion of 3 to 4 and the sulfur(II) transfer in the conversion of 5 to 6 are found to be intermolecular. These results are taken to be consistent with transition structures for these sulfur transfer reactions which require a large angle between the entering and leaving group, a geometry analogous to apical group positions in trigonal bipyramidal transition states.
A mild inter- and intramolecular amination of aryl halides with a combination of CuI and CsOAc
Kubo, Tetsuji,Katoh, Chiharu,Yamada, Ken,Okano, Kentaro,Tokuyama, Hidetoshi,Fukuyama, Tohru
supporting information; experimental part, p. 11230 - 11236 (2009/04/11)
A unique combination of CuI and CsOAc was found to catalyze aryl amination under mild conditions. The reaction takes place at room temperature or at 90 °C with broad functional group compatibility. The intramolecular reaction was able to form five-, six-, and seven-membered rings with various protecting groups on the nitrogen atom. The scope of the intermolecular amination, as well as its applications to unsymmetrical N,N′-dialkylated phenylenediamines, was investigated.
Synthesis of indolines and tetrahydroisoquinolines from arylethylamines by PdII-catalyzed C-H activation reactions
Li, Jiao-Jie,Mei, Tian-Sheng,Yu, Jin-Quan
scheme or table, p. 6452 - 6455 (2009/03/11)
(Chemical Equation Presented) Hand in hand: A versatile C-H activation route for the synthesis of indolines, tetrahydroquinolines, and tetrahydroisoquinolines from simple arylethylamines relies on a one-pot iodination and amination reaction (see scheme, Tf=trifluoromethanesulfonyl). The natural amino acids phenylalanine, tyrosine, and tryptophan can be converted into various heterocycles by using this technology.
