32487-03-9Relevant academic research and scientific papers
Succinct Syntheses of Methopholine, (±)-Homolaudanosine, and (±)-Dysoxyline via Metal-free One-Pot Double Alkylation on 1-Methyl-3,4-dihydroisoquinolines
Achary, Raghavendra,Kim, Seulgi,Choi, Yuri,Mathi, Gangadhar Rao,Kim, Hyun Jin,Hwang, Jong Yeon,Kim, Pilho
, p. 270 - 278 (2019/02/20)
A mild one-pot and metal-free condition was discovered to implement two different alkyl groups chemoselectively on 1-methyl-3,4-dihydroisoquinoline (1-Me-DHIQ), one at the nitrogen another at the C1-methyl group. This chemistry is compatible with various DHIQs as well as alkyl halides. Application of this chemistry facilitated the concise syntheses of methopholine, (±)-homolaudanosine, and (±)-dysoxyline, requiring only two steps from 6,7-dimethoxy-1-Me-DHIQ.
Unified approach to isoindolinones and THIQs via lewis acid catalyzed domino mukaiyama-mannich Lactamization/Alkylations: Application in the synthesis of (±)-homolaudanosine
Dhanasekaran, Sivasankaran,Kayet, Anirban,Suneja, Arun,Bisai, Vishnumaya,Singh, Vinod K.
, p. 2780 - 2783 (2015/06/16)
A novel and efficient synthesis of a variety of isoindolinones and tetrahydroisoquinolines via a Lewis acid catalyzed domino Mukaiyama-Mannich lactamization/alkylation is achieved. This transformation comprises a sequential formation of three new bonds through a one-pot, three-component procedure to afford product in moderate to high yields. A concise synthesis of (±)-homolaudanosine (2b) has been achieved using this method.
C-1 alkynylation of N-methyltetrahydroisoquinolines through CDC: A direct access to phenethylisoquinoline alkaloids
Singh, Kamal Nain,Singh, Paramjit,Kaur, Amarjit,Singh, Pushpinder
, p. 760 - 764 (2012/07/02)
Direct cross-coupling between N-methyltetrahydroisoquinolines and alkynes using CuI-DEAD is presented. It affords the regioselective C-1-alkynylated products in good yield. This regio-selectivity is in contrast to the results reported earlier in the reaction of N,N-dimethylbenzyl amine where the N-methyl alkynylated product was formed exclusively or predominantly. The C-1-substituted propargylic isoquinolines were easily reduced to phenethylisoquinolines with Pd/C. This reaction sequence provides a short route to synthesize methopholine, homolaudanosine and other phenethylisoquinoline alkaloids. Georg Thieme Verlag Stuttgart · New York.
Synthesis and radioligand binding studies of methoxylated 1,2,3,4-tetrahydroisoquinolinium derivatives as ligands of the apamin-sensitive Ca2+-activated K+ channels
Graulich, Amaury,Scuvée-Moreau, Jacqueline,Alleva, Livia,Lamy, Cédric,Waroux, Olivier,Seutin, Vincent,Liégeois, Jean-Fran?ois
, p. 7208 - 7214 (2007/10/03)
Several methoxylated 1,2,3,4-tetrahydroisoquinoliniums derived from N-methyl-laudanosine and N-methyl-noscapine were synthesized and evaluated for their affinity for apamin-sensitive binding sites. The quaternary ammonium derivatives have a higher affinit
Ruthenium dioxide in fluoro acid medium. III. Aplication to the synthesis of aporphinic, homoaporphinic and dibenzazocinic alkaloids. Studies towards the preparation of azafluoranthenic skeleton
Landais,Robin
, p. 7185 - 7196 (2007/10/02)
Intramolecular oxidative couplings of phenylalkyltetrahydroisoquinoline precursors in aporphinic and homoaporphinic alkaloids by using RuO2,2H2O in fluoro acidic media were performed. A comparative study of our reagent with TTFA has been made with different precursors. The procedure was also extended to the synthesis of one dibenzazocinic alkaloid. Then, we attempted to synthetize the azafluoranthenic ring, using phenolic and non phenolic isoquinoline precursors.
The E.S.R. Spectra of Cation Radicals Derived from Phenethyltetrahydroisoquinoline Ethers and Model Compounds
Hewgill, Frank R.,Pass, Michael C.
, p. 555 - 563 (2007/10/02)
Cation radicals derived from the title compounds by oxidation with thallium tristrifluoroacetate have been characterized.The structures assigned to these radicals suggest that initial oxidation occures at the phenethyl ring in the compounds examined.Oxidation of homolaudanosine in this way gave the expected homoaporphine.
