- Light-Induced Alkylation of (Hetero)aromatic Nitriles in a Transition-Metal-Free C-C-Bond Metathesis
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A light-induced C-C-σ-bond metathesis was achieved through transition-metal-free activation of an unstrained C(sp3)-C(sp3)-σ-bond in 1-benzyl-1,2,3,4-tetrahydroisoquinolines. A photoredox-mediated single-electron oxidation of these precursor amines yield radical cations which undergo a homolytic cleavage of a C(sp3)-C(sp3)-σ-bond rather than the well-known α-C-H-scission. The resulting carbon-centered radicals are used in the ipso-substitution of (hetero)aromatic nitriles proceeding through another single-electron transfer-mediated C-C-bond cleavage and formation.
- Lipp, Benjamin,Lipp, Alexander,Detert, Heiner,Opatz, Till
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supporting information
p. 2054 - 2057
(2017/04/27)
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- Enantioselective Oxidative Aerobic Dealkylation of N-Ethyl Benzylisoquinolines by Employing the Berberine Bridge Enzyme
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N-Dealkylation methods are well described for organic chemistry and the reaction is known in nature and drug metabolism; however, to our knowledge, enantioselective N-dealkylation has not been yet reported. In this study, exclusively the (S)-enantiomers o
- Gandomkar, Somayyeh,Fischereder, Eva-Maria,Schrittwieser, Joerg H.,Wallner, Silvia,Habibi, Zohreh,Macheroux, Peter,Kroutil, Wolfgang
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p. 15051 - 15054
(2016/01/25)
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- Synthesis of (+)-O-methylthalibrine by employing a stereocontrolled Bischler-Napieralski reaction and an electrochemically generated diaryl ether
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An efficient electrochemical four-step route was developed for the preparation of diaryl ether derivatives by using halogenation and dehalogenation processes in addition to electrochemical phenolic oxidation and reduction reactions. The synthesis of (+)-O
- Kawabata, Yuki,Naito, Yu,Saitoh, Tsuyoshi,Kawa, Kohei,Fuchigami, Toshio,Nishiyama, Shigeru
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- A new benzylisoquinoline alkaloid from Argemone mexicana
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A new benzylisoquinoline alkaloid, argemexirine, together with two known protoberberine alkaloids, dl-tetrahydrocoptisine and dihydrocoptisine, have been isolated from the methanolic extract of the whole plant of Argemone mexicana L. The compounds were identified by spectral and chemical evidence. This is the first report of these alkaloids in this plant species.
- Singh, Sarita,Singh,Singh,Pandey
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experimental part
p. 63 - 67
(2010/04/23)
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- Effect of isoquinoline alkaloids of different structural types on antiplatelet aggregation in vitro
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Forty-one isoquinoline alkaloids were tested for antiplatelet aggregation effects. Among them, (-)-discretamine (6), protopine (7), ochotensimine (18), O-methylarmepavinemethine (23), lindoldhamine (25), isotetrandrine (26), thalicarpine (27), papaverine (28), and D-(+)-N-norarmepavine (32) exhibited significant inhibitory activity towards adenosine 5′-diphosphate (ADP)-, arachidonic acid (AA)-, collagen-, and/or platelet-activating factor (PAF)-induced platelet aggregation. The results are discussed on the basis of structure-activity relationships. Georg Thieme Verlag KG Stuttgart.
- Chia, Yi-Chen,Chang, Fang-Rong,Wu, Chin-Chung,Teng, Che-Ming,Chen, Keh-Shaw,Wu, Yang-Chang
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p. 1238 - 1241
(2007/10/03)
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- Method and health food for preventing and/or alleviating psychiatric disorder, and/or for effectuating sedation
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A method for preventing and/or alleviating a psychiatric disorder, and/or effectuating sedation, comprising administering a benzylisoquinoline derivative represented by General Formula (I): wherein R1, R2, R3 and X each re
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Page/Page column 9
(2008/06/13)
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- Syntheses of the seco benzyltetrahydroisoquinoline alkaloids polysignine and methoxypolysignine
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The structures previously assigned to the seco benzyltetrahydroisoquinoline alkaloids polysignine (1) and methoxypolysignine (2) have been confirmed by total syntheses in which the key step involved cleavage of the C 1-N bonds in the corresponding N-methylbenzyltetrahydroisoquinolines. CSIRO 2000.
- Nimgirawath, Surachai
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p. 523 - 525
(2007/10/03)
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- Novel Zinc-Promoted Alkylation of Iminium Salts. New Synthesis of Benzylisoquinoline, Phthalidylisoquinoline, and Protoberberine Alkaloids and Related Compounds
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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.
- Shono, Tatsuya,Hamaguchi, Hiroshi,Sasaki, Manji,Fujita, Shumei,Nagami, Kimihiko
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p. 1621 - 1628
(2007/10/02)
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- SYTHESIS OF N-(ARYLETHYL)ARYLTHIOACETAMIDES BY THE WILLGERODT-KINDLER REACTION AND THEIR CONVERSION TO SUBSTITUTED 1-BENZYL-1,2,3,4-TETRAHYDROISOQUINOLINES
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N-(Arylethyl)arylthioacetamides were synthesized by the reaction of substituted acetophenones with 2-arylethylamines.The reaction gives good yields when compounds with substituted hydroxyl groups are used. 2,4-Diarylthiazoles were isolated as side products from the Wilgerodt-Kindler reaction.The thioamides were converted into substituted 1-benzyl-1,2,3,4-tetrahydroisoquinolines by the Bischler-Napieralski cyclization, N-methylation, and reduction of the corresponding 3,4-dihydroisoquinoline methiodide derivatives.
- Nakova, E.P.,Tolkachev, O.N.,Evstigneeva, R.P.
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p. 550 - 555
(2007/10/02)
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