Relevant bibliographies by topics / Bischler napieralski reaction

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Academic literature on the topic 'Bischler napieralski reaction'

Author: Grafiati
Published: 4 June 2021
Last updated: 3 February 2022

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Journal articles on the topic "Bischler napieralski reaction"

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Puerto Galvis, Carlos, Mario Macías, and Vladimir Kouznetsov. "Unexpected PF6 Anion Metathesis during the Bischler–Napieralski Reaction: Synthesis of 3,4-Dihydroisoquinoline Hexafluorophosphates and Their Tetrahydroisoquinoline Related Alkaloids." Synthesis 51, no. 09 (February 18, 2019): 1949–60. http://dx.doi.org/10.1055/s-0037-1610684.

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A series of N-phenethylcinnamamides were subjected to the Bischler–Napieralski reaction to furnish diverse 1-styryl-3,4-dihydroisoquinolines. We noticed that the desired products were unstable when the reaction was performed under conventional solvent conditions. However, when [bmim]PF6 was used as the reaction media, the nature of the Bischler–Napieralski reaction promoted an unusual in situ ionic interchange between this ionic liquid and the dihydroisoquinoline core that led to the stabilization of the desired 1-styryl-3,4-dihydroisoquinolines, allowing their isolation as hexafluorophosphate salts. Finally, the one-pot reduction/reductive methylation process afforded the N-methyl derivatives, establishing that our findings can be an efficient and useful strategy for the concise synthesis of tetrahydroisoquinoline alkaloids.
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Kim, Kyung-Hee, and Cheol-Hong Cheon. "Concise catalytic asymmetric total syntheses of ancistrocladinium A and its atropdiastereomer." Organic Chemistry Frontiers 4, no. 7 (2017): 1341–49. http://dx.doi.org/10.1039/c7qo00195a.

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Ishikawa, Tsutomu, Tatsuru Saito, and Makoto Yoshida. "Triphosgene: A Versatile Reagent for Bischler-Napieralski Reaction." HETEROCYCLES 54, no. 1 (2001): 437. http://dx.doi.org/10.3987/com-00-s(i)44.

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Ramesh, D., and M. Srinivasan. "Phosphonitrilic Chloride - A Reagent for Bischler-Napieralski Reaction." Synthetic Communications 16, no. 12 (October 1986): 1523–27. http://dx.doi.org/10.1080/00397918608056405.

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Abu-Safieh, Kayed A., Mustafa M. El-Abadelah, Salim S. Sabri, Wolfgang Voelter, Cäcilia M. Mössmer, and Markus Stroebele. "Bischler-Napieralski Synthesis of Some New Pyrazole-Fused β-Carbolines." Zeitschrift für Naturforschung B 57, no. 11 (November 1, 2002): 1327–32. http://dx.doi.org/10.1515/znb-2002-1120.

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3-(4-Acylaminopyrazol-5-yl)-4-methylindoles (13a,b), under Bischler-Napieralski reaction conditions, undergo cyclization at the pyrrolic carbon-2 with ultimate formation of the corresponding pyrazolo[3,4:5′,6′]pyrido[3,4-b]indoles (14a,b) as evidenced by crystal structure analysis of 14a.
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Muratov, A. V., S. A. Grebenyuk, and A. B. Eresko. "Synthesis of 1,2-Diazepines by the Bischler–Napieralski Reaction." Russian Journal of Organic Chemistry 54, no. 6 (June 2018): 861–66. http://dx.doi.org/10.1134/s1070428018060064.

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Meruva, Suresh Babu, Akula Raghunadh, Raghavendra Rao Kamaraju, U. K. Syam Kumar, and P. K. Dubey. "An oxidative amidation and heterocyclization approach for the synthesis of β-carbolines and dihydroeudistomin Y." Beilstein Journal of Organic Chemistry 10 (February 25, 2014): 471–80. http://dx.doi.org/10.3762/bjoc.10.45.

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A novel synthetic methodology has been developed for the synthesis of dihydro-β-carboline derivatives employing oxidative amidation–Bischler–Napieralski reaction conditions using tryptamine and 2,2-dibromo-1-phenylethanone as key starting materials. A number of dihydro-β-carboline derivatives have been synthesized in moderate to good yields using this methodology. Attempts were made towards the conversion of these dihydro-β-carbolines to naturally occurring eudistomin alkaloids.
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Han, Yi, Zhenzhu Hu, Meifang Liu, Mengwei Li, Tingting Wang, and Yulan Chen. "Synthesis, Characterization, and Properties of Diazapyrenes via Bischler–Napieralski Reaction." Journal of Organic Chemistry 84, no. 7 (February 26, 2019): 3953–59. http://dx.doi.org/10.1021/acs.joc.8b03096.

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Syam Kumar, U., R. Shankar, Satish More, M. Madhubabu, and N. Vembu. "Synthesis of Isoquinoline Alkaloids via Oxidative Amidation-Bischler-Napieralski Reaction." Synlett 23, no. 07 (March 28, 2012): 1013–20. http://dx.doi.org/10.1055/s-0031-1290655.

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Saito, Tatsuru, Makoto Yoshida, and Tsutomu Ishikawa. "ChemInform Abstract: Triphosgene: A Versatile Reagent for Bischler-Napieralski Reaction." ChemInform 32, no. 23 (May 26, 2010): no. http://dx.doi.org/10.1002/chin.200123139.

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Dissertations / Theses on the topic "Bischler napieralski reaction"

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White, Kolby Lyn. "Mechanistic investigation of the interrupted Bischler-Napieralski reaction and its application to the total synthesis of the aspidosperma alkaloids." Thesis, Massachusetts Institute of Technology, 2017. http://hdl.handle.net/1721.1/109682.

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Thesis: Ph. D. in Organic Chemistry, Massachusetts Institute of Technology, Department of Chemistry, 2017.
Vita. Scanning issues: Page 114 contains text that has been cropped/deleted from the right-side page margin. Appendix B section contains several graph pages with faint/illegible images. Cataloged from PDF version of thesis.
Includes bibliographical references.
I. Direct Observation of Intermediates Involved in the Interruption of the Bischler- Napieralski Reaction. The first mechanistic investigation of electrophilic amide activation of [alpha], [alpha]-disubstituted tertiary lactams and the direct observation of key intermediates by in situ FTIR, 1H, 13C, and 19F NMR in our interrupted Bischler-Napieralski based synthetic strategy to the aspidosperma alkaloids is described. Importantly, when considering base additives during electrophilic amide activation, more hindered c-quaternary tertiary lactams require the use of non-nucleophilic pyridine additives in order to avoid deactivation via a competing desulfonylation reaction. The isolation and full characterization of a tetracyclic iminium trifluoromethanesulfonate provided additional correlation between in situ characterization of sensitive intermediates and isolable compounds involved in this synthetic transformation. II. Total Synthesis of (+)-Fendleridine, (+)-Acetylaspidoalbidine, and (+)-Limaspermidine. An Tf2O-mediated electrophilic amide activation of a readily available C21-oxygenated lactam, followed by transannular cyclization and in situ trapping of a transiently formed C19-iminium ion, expediently provides access to the hexacyclic C19-hemiaminal ether alkaloids (+)- fendleridine, (+)-acetylaspidoalbidine, and (+)-limaspermidine. A highly effective enzymatic resolution of a non-[beta]-branched primary alcohol (E=22) allowed rapid preparation of both enantiomeric forms of a C21-oxygenated precursor for synthesis of these aspidosperma alkaloids. III. Development of an Ortho-Acetoxylation of Indoline Amides and its Application to the Total Synthesis of (+)-Haplocidine and (+)-Haplocine. The first total syntheses of (+)-haplocidine and its NI-amide congener (+)-haplocine is described. The concise synthesis of these alkaloids required the development of a late-stage and highly selective C-H oxidation of complex aspidosperma alkaloid derivatives. A versatile, amide directed ortho-acetoxylation of indoline amides enabled the implementation of a unified strategy for late-stage diversification of hexacyclic C19-hemiaminal ether structures via oxidation of the corresponding pentacyclic C19-iminium ions.
by Kolby Lyn White.
Ph. D. in Organic Chemistry
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2

Medley, Jonathan William. "Direct dehydrative N-Pyridinylation of amides, the interrupted Bischler-Napieralski reaction, and the enantioselective total synthesis and arylative dimerization of aspidosperma alkaloids." Thesis, Massachusetts Institute of Technology, 2013. http://hdl.handle.net/1721.1/82319.

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Thesis (Ph. D. in Organic Chemistry)--Massachusetts Institute of Technology, Dept. of Chemistry, 2013.
Cataloged from PDF version of thesis. Vita.
Includes bibliographical references.
I. Direct Dehydrative N-Pyridinylation of Amides A method for the single-step N-pyridinylation of secondary amides is described. The process involves electrophilic activation of secondary amides with trifluoromethanesulfonic anhydride in the presence of 2-fluoropyridine followed by introduction of a pyridine N-oxide derivative and warming to afford the corresponding N-pyridinyl tertiary amide derivatives. The structure of activated amide intermediates is probed through in situ monitoring, and a mechanism supported by in situ monitoring and deuterium labeling experiments is discussed. II. Synthesis of Spirocyclic Indolines by Interruption of the Bischler-Napieralski Reaction The development of a versatile method for the synthesis of spirocyclic pyrrolidinoindolines is described. Treatment of N-acyltryptamines with trifluoromethanesulfonic anhydride-2-chloropyridine reagent combination affords highly persistent spiroindoleninium ions, which are selectively trapped intra- and intermolecularly by various nucleophiles. III. A Concise and Versatile Double-Cyclization Strategy for the Highly Stereoselective Synthesis and Novel Arylative Dimerization of Aspidosperma Alkaloids A strategy for the concise, stereoselective synthesis of aspidosperma alkaloids and related structures via a common putative diiminium ion intermediate is described. The approach enables the dimerization of aspidosperma-type structures at the sterically hindered C2-position. The diiminium intermediate is prepared in situ from an enantioenriched [alpha]-quaternary 2- chlorotryptamine lactam through a stereoselective electrophilic double-cyclization cascade. The key C5-quaternary stereocenter is secured via successive diastereoselective [alpha]-alkylations of pseudoephenamine crotonamide.
by Jonathan William Medley.
Ph.D.in Organic Chemistry
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Haelters, Jean-Pierre. "Synthèse de dérivés phosphono-indoliques-benzofuranniques et -pyrroliques à partir d'hydrazones phosphonates." Brest, 1987. http://www.theses.fr/1987BRES2002.

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Des derives phosphonoindoliques sont prepares par cyclisation d'arylhydrazones d'oxoalkylphosphonates selon fisher et par cyclodeshydratation d'arylamino-1 et arylamino-3 oxo-2 propylphosphonates selon bischler. Des indolyl-2 et indolyl-3 phosphonates, des indolylmethyl-2 et des indolylmethyl-3 phosphonates diversement substitues et leurs acides phosphoniques correspondants sont decrits. Toutes structures sont analysees par rmn **(1)h, **(31)p et 1**(3)c. L'analogue phosphore de l'intermediaire a aussi ete prepare. L'extention de la reaction de bischler aux aryloxycetones permet d'atteindre des benzofuryl-2 phosphonate et de benzofurylmethyl-3 phosphonates. Deux nouveaux reactifs sont utilises pour acceder aux arylaminocetones et aux aryloxycetones : les chloro-1 et chloro-3 methoxycarbonylhydrazono-2 propyl-phosphonates de diethyle, composes qui, traites en milieu basique, donnent des azoenes qui additionnent les anilines et les phenols. Ces azoenes additionnent aussi les carbanions, notamment les carbanions derives de cetones pour conduire, apres hydrolyse soit a des derives du pyrrole, soit a des dioxy-2, -5-alkylphosphonates precurseurs de cyclopentenones selon wittig-horner
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Book chapters on the topic "Bischler napieralski reaction"

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Li, Jie Jack. "Bischler-Napieralski reaction." In Name Reactions, 36. Berlin, Heidelberg: Springer Berlin Heidelberg, 2002. http://dx.doi.org/10.1007/978-3-662-04835-1_28.

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Li, Jie Jack. "Bischler–Napieralski reaction." In Name Reactions, 48–49. Berlin, Heidelberg: Springer Berlin Heidelberg, 2009. http://dx.doi.org/10.1007/978-3-642-01053-8_23.

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Li, Jie Jack. "Bischler–Napieralski reaction." In Name Reactions, 56–57. Cham: Springer International Publishing, 2014. http://dx.doi.org/10.1007/978-3-319-03979-4_27.

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Li, Jie Jack. "Bischler-Napieralski reaction." In Name Reactions, 39. Berlin, Heidelberg: Springer Berlin Heidelberg, 2003. http://dx.doi.org/10.1007/978-3-662-05336-2_30.

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Li, Jie Jack. "Bischler–Napieralski Reaction." In Name Reactions, 44–46. Cham: Springer International Publishing, 2021. http://dx.doi.org/10.1007/978-3-030-50865-4_15.

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Heravi, Majid M., Soheila Khaghaninejad, and Niousha Nazari. "Bischler–Napieralski Reaction in the Syntheses of Isoquinolines∗." In Advances in Heterocyclic Chemistry, 183–234. Elsevier, 2014. http://dx.doi.org/10.1016/b978-0-12-800171-4.00005-6.

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