841-95-2Relevant academic research and scientific papers
Quinolizidine compound and the manufacturing method thereof
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, (2021/02/19)
Provided are benzoquinolizidine and indoloquinolizidine derivative compounds prepared by performing Mannich reaction using Azza-Michahael response and DDQ oxidizer from tetrahydroisoquinoline or tryptoline, and to a process for preparing the same. The met
Sequential One-Pot Vilsmeier-Haack and Organocatalyzed Mannich Cyclizations to Functionalized Benzoindolizidines and Benzoquinolizidines
Outin, Johanne,Quellier, Pauline,Bélanger, Guillaume
, p. 4712 - 4729 (2020/03/30)
The development of new one-pot sequential cyclizations involving a Vilsmeier-Haack reaction followed by an organocatalyzed Mannich reaction is reported. This synthetic strategy gives access to functionalized indolizidines and quinolizidines in one operation from readily synthesized precursors. Yields and diastereoselectivities are good to excellent when formamides are used to trigger the key step, bearing either an electron-rich aryl or a pyrrole as the nucleophilic partner in the first cyclization.
Synthesis of (±)-Tetrabenazine by Visible Light Photoredox Catalysis
Orgren, Lindsey R.,Maverick, Emily E.,Marvin, Christopher C.
, p. 12635 - 12640 (2016/01/09)
(±)-Tetrabenazine was synthesized in six steps from commercially available compounds. The key cyclization substrate was assembled rapidly via Baylis-Hillman and aza-Michael reactions. Annulation of the final ring was achieved through visible light photocatalysis, wherein carbon-carbon bond formation was driven by the oxidation of a tertiary amine. Solvent played a critical role in the photoredox cyclization outcome, whereas methanol led to a mixed ketal, acetonitrile/water (10:1) gave direct cyclization to (±)-tetrabenazine and occurred more rapidly.
A new route to heterocyclic compounds by the mercuric acetate oxidation of N-alkyl substituted 4-piperidones
Flick, Andrew C.,Padwa, Albert
, p. 5739 - 5741 (2008/12/22)
N-Alkyl substituted 4-piperidones readily undergo oxidation in high yield upon reaction with mercuric acetate. Application of the oxidation to the synthesis of the skeletal framework of several alkaloids is described.
NEW SYNTHESIS OF BENZOQUINOLIZIDIN-2-ONES via PROTECTED 2-ARYL-4-PIPERIDONES
Rubiralta, Mario,Diez, Anna,Balet, Antonia,Bosch, Joan
, p. 3021 - 3030 (2007/10/02)
A new synthesis of 9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-benzoquinolizin-2-one (1a) and its 3-ethyl derivative 1b via the corresponding 2-(3,4-dimethoxyphenyl)-4-piperidone ethylene acetals 7 is reported.Alkylation of 2-arylpiperidines 7 with 2-bro
Novel Zinc-Promoted Alkylation of Iminium Salts. New Synthesis of Benzylisoquinoline, Phthalidylisoquinoline, and Protoberberine Alkaloids and Related Compounds
Shono, Tatsuya,Hamaguchi, Hiroshi,Sasaki, Manji,Fujita, Shumei,Nagami, Kimihiko
, p. 1621 - 1628 (2007/10/02)
Zinc-promoted reductive coupling reaction of iminium salts with alkyl halides was found to be a successful key reaction for synthesis of a variety of alkaloids such as benzylisoquinoline, phthalidylisoquinoline, and protoberberine alkaloids.More specifically, laudanosine, cordrastine, hydrastine, narcotine, tetrahydropalmatine, and canadine were obtained.A new route for the synthesis of the emetine and yohimbine skeletons was exploited.
Synthesis and Antihypertensive Activity of a Series of Spiroquinolizine-2,5'-oxazolidin-2'-one>s
Caroon, Joan M.,Clark, Robin D.,Kluge, Arthur F.,Lee, Chi-Ho,Strosberg, Arthur M.
, p. 1426 - 1433 (2007/10/02)
The 2R*,11bS* and 2S*,11bS* diastereoisomers of the spiroquinolizine-2,5'-oxazolidin-2'-one> system were prepared by stereoselective methods.Evaluation of these compounds for antihypertensive activity by oral administration to the spontaneously hypertensive rat showed the 2S*,11bS* series was the more potent.Within that series it was found that small alkyl substituents at positions 3 and 4' enhanced antihypertensive activity and that methoxyl substitution at positions 9 and 10 was optical. (2S,3S,11bS)-Spiroquinolizine-2,5'-oxazolidin-2'-one> was one of the most efficacious compounds of this series, while its antipode, (+)-9e, was inactive.Selected compounds in this series were shown to be α-adrenoceptor antagonists.
