154138-43-9Relevant academic research and scientific papers
Direct Synthesis of Protoberberine Alkaloids by Rh-Catalyzed C-H Bond Activation as the Key Step
Jayakumar, Jayachandran,Cheng, Chien-Hong
supporting information, p. 1800 - 1804 (2016/02/20)
A one-pot reaction of substituted benzaldehydes with alkyne-amines by a Rh-catalyzed C-H activation and annulation to afford various natural and unnatural protoberberine alkaloids is reported. This reaction provides a convenient route for the generation o
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
Asymmetric synthesis of 1-vinyltetrahydroisoquinoline through Pd-catalyzed intramolecular allylic amination
Shi, Ce,Ojima, Iwao
, p. 8563 - 8570 (2008/02/08)
Asymmetric synthesis of 6,7-dimethoxy-1-vinyltetrahydroisoquinolines through Pd-catalyzed intramolecular allylic amination of 3-(amidoethylphenyl)prop-2-enyl carbonates was studied, using a library of fine-tunable monodentate phosphoramidite ligands. Unde
Enantioselective synthesis of (+)-(S)-laudanosine and (-)-(S)-xylopinine
Mujahidin, Didin,Doye, Sven
, p. 2689 - 2693 (2007/10/03)
The study presents a new pathway for the enantioselective synthesis of benzylisoquinoline alkaloids. The key steps of the synthesis of (+)-(S)-laudanosine (1) and (-)-(S)-xylopinine (2) are a Sonogashira coupling that builds up the C1-C8a bond of the benzylisoquinoline skeleton, an intramolecular Ti-catalyzed hydroamination of an alkyne, and a subsequent enantioselective imine reduction according to Noyori's protocol.
Asymmetric Intramolecular Allylic Amination: Straightforward Approach to Chiral C1-Substituted Tetrahydroisoquinolines
Ito, Katsuji,Akashi, Suemi,Saito, Bunnai,Katsuki, Tsutomu
, p. 1809 - 1812 (2007/10/03)
Newly introduced Pd-catalyzed asymmetric intramolecular allylic amination provides an easy access to pharmaceutically important 1-substituted tetrahydroisoquinolines. With this amination as the key step, (R)-carnegine was synthesized in an enantioselectiv
A direct iodination method with iodine and silver triflate for the synthesis of SPECT and PET imaging agent precursors
Mulholland,Zheng
, p. 3059 - 3068 (2007/10/03)
A direct iodination method with iodine and silver triflate for the synthesis of SPECT and PET imaging agent precursors has been developed.
Regioselective synthesis of 6-fluorodopamine, 6-fluoro-m-tyramine and 4-fluoro-m-tyramine using elemental fluorine, oxygen difluoride and acetyl hypofluorite
Namavari, Mohammad,Satyamurthy, N.,Barrio, Jorge R.
, p. 113 - 122 (2007/10/03)
6-Fluorodopamine was regioselectively synthesized in good yields from N-(trifluoroacetyl)-3,4-di-t-butoxycarbonyloxy-6-(trimethylstannyl)phenylethylamine (6) via a fluorodestannylation reaction using F2, OF2 or CH3COOF followed by acid hydrolysis.Similarly, 6-fluoro-m-tyramine (14) and 4-fluoro-m-tyramine (20) were prepared from their corresponding trimethylstannyl derivatives.All precursors and products were fully characterized by multinuclear NMR spectroscopy and high resolution mass spectrometry. - Keywords: Dopamine neurotransmission; Norepinephrine synthesis; Dopamine agonist; 6-fluorodopamine; Fluorodestannylation
Efficient synthesis of 2,3,4,5-tetrahydro-1H-3-benzazepines by intramolecular Heck reaction
Tietze,Schimpf
, p. 876 - 880 (2007/10/02)
A new facile method for the synthesis of the pharmacologically interesting 3-benzazepine skeleton is described. The easily available iodinated benzene derivative 3 is alkylated with allyl halides 4a-c to afford compounds 5a-c. Pd-catalyzed Heck-type cycli
