66384-45-0Relevant academic research and scientific papers
Preparation method of compound 5,6-dihydroxy indoline and halogen acid salts thereof
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Paragraph 0074-0077, (2018/04/01)
The invention relates to a preparation method of a compound 5,6-dihydroxy indoline and halogen acid salts thereof. Phenylethylamine SM-0 sold in the market is used as a raw material and firstly reactswith acyl chloride to obtain amide SM-1; amide SM-1 rea
Catechol reactivity: Synthesis of dopamine derivatives substituted at the 6-position
Rote, Jennifer C.,Malkowski, Sarah N.,Cochrane, C. Skyler,Bailey, Gabrielle E.,Brown, Noah S.,Cafiero, Mauricio,Peterson, Larryn W.
supporting information, p. 435 - 441 (2017/02/24)
Dopamine is a ubiquitous neurotransmitter essential in the proper functioning of the human body. In addition to this critical role, the catecholamine core has shown utility as a scaffold for numerous drugs and in other applications, like metal detection and adhesive materials. Substituents at the 6-position of dopamine’s catechol core can modulate its stereoelectronic properties, the acidity of its phenolic hydroxyl groups, and the overall hydrophobicity of the molecule. Herein, we report the synthesis of a series of four novel dopamine analogues substituted at the 6-position of catechol core. The1H NMR chemical shift of the aromatic proton meta to the substituent correlated strongly with the Hammett σmconstant, confirming the electronic properties of substituents.
A ring-closing metathesis-based approach to the synthesis of (+)-tetrabenazine
Johannes, Manuel,Altmann, Karl-Heinz
supporting information; experimental part, p. 3752 - 3755 (2012/09/07)
A modular stereoselective synthesis of the vesicular monoamine transport inhibitors (+)-tetrabenazine ((+)-1) and (+)-α-dihydrotetrabenazine ((+)-2) has been developed. The approach is based on amine 4 and acid 5 as the key building blocks, which were elaborated into macrolactam 3 by amide coupling and a subsequent highly E-selective RCM reaction. Macrolactam 3 could be converted into tetrabenazine in three known steps.
Phosphane-free Pd0-catalyzed cycloamination and carbonylation with Pd(OAc)2 and Cu(OAc)2 in the presence of K 2CO3: Preparation of benzocyclic amines and benzolactams
Harada, Rika,Nishida, Naoto,Uchiito, Shiho,Onozaki, Yu,Kurono, Nobuhito,Senboku, Hisanori,Masao, Tokuda,Ohkuma, Takeshi,Orito, Kazuhiko
experimental part, p. 366 - 379 (2012/02/04)
Phosphane-free Pd0-catalyzed intramolecular aromatic amination was studied. o-Halophenethylamines and 3-(o-halophenyl)propylamines were found to be transformed into indolines and quinolines in a catalytic system based on Pd(OAc)2 and Cu(OAc)2 in the presence of K 2CO3. Application of the method to substrates containing isoquinoline rings- the 1-(o-bromobenzyl)-3,4-dihydroisoquinolines 6, the 1-(o-bromobenzyl)-1,2,3,4-tetrahydroisoquinolines 7, and the 1-(o-bromophenethyl)isoquinolines 9- provided the indolo[2,1-a]isoquinoline and dibenzo[a,f]quinolizine ring systems 8 and 10. Extension of the method to β-carbolines (compounds 11, 12, and 17) produced the benz[f]indolo[2,3-a] indolizine-13-ones 15 and the benz[f]indolo[2,3-a]quinolizine 18. The benzo[f]pyrido[3,4-a]indolizine and indolo[f]pyrido[3,4-a]indolizin-12-one ring systems 27 and 31 were built in a similar manner. It was also found that under an atmosphere of CO the same catalytic system produced the corresponding benzolactams, the isoquino[2,1-a][2,7]naphthyridine 34 and the indolo[2,3-a]pyrido[g]quinolizin-8-one 36 [(±)-dihydronauclefine] in good yields. Copyright
Application of the ortho-Lithiation-Cyclization Strategy to N-Benzyl- and N-Phenethylamine Derivatives
Lete, Esther,Collado, M. Isabel,Sotomayor, Nuria,Vicente, Teresa,Villa, Maria-Jesus
, p. 1751 - 1758 (2007/10/03)
The ortho-lithiation-cyclization of iodinated N,N-diacylphenethylamines provides a convenient method for the preparation of 2-(2-acetoamidoethyl)acetophenones and 2-(2-benzamidoethyl)benzophenones, which could be easily transformed into dihydroisoquinolines.By contrast, the N-ethylamino, N-acetylamino, and N-trimethylsilylamino moieties studied as ortho-directing groups provide poor assistance to the metalation of N-benzyl- and N-phenyethylamines and the corresponding isoindolone or isoquinolone derivatives are obtained in low yields.
Iodination of alkyl aryl ethers by mercury(II) oxide-iodine reagent in dichloromethane
Orito,Hatakeyama,Takeo,Suginome
, p. 1273 - 1277 (2007/10/02)
A convenient method for selective mono- and diiodination of alkyl aryl ethers by mercury(II) oxide-iodine reagent in dichloromethane is reported.
