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Synthesis Of Tricyclic Benzazocines By Aza-Prins Reaction.

Tomohiro Katamura, Tomoaki Shimizu, Y. Mutoh, S. Saito
Published 2017 · Chemistry, Medicine

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The aza-Prins reaction of 3-vinyltetrahydroquinolines with aldehydes proceeded smoothly in the presence of hydrogen halides, and the tricyclic benzazocine derivatives were isolated in good to high yields. The reaction would proceed through the formation and cyclization of the iminium ion intermediate.
This paper references
10.3987/COM-12-S(N)78
AN EFFECTIVE PROCEDURE TO PROMOTE AZA-PRINS CYCLIZATION REACTIONS EMPLOYING A COMBINATION OF FERRIC CHLORIDE AND AN IMIDAZOLIUM SALT IN BENZOTRIFLUORIDE
Chika Osawa (2012)
10.1002/EJOC.201402971
Toward Pyridine–Heterocycle Patterns through Prins and Aza-Prins Cyclisations: Application to a Short Synthesis of (±)-Anabasine
O. Colin (2014)
10.1002/anie.201404191
Bioinspired total synthesis of sespenine.
Y. Sun (2014)
10.1021/acs.joc.5b02342
Synergistic Effect of the TiCl4/p-TsOH Promoter System on the Aza-Prins Cyclization.
Vianney Durel (2016)
10.3762/bjoc.6.41
Prins fluorination cyclisations: Preparation of 4-fluoro-pyran and -piperidine heterocycles
Guillaume G Launay (2010)
10.1002/asia.201200505
Asymmetric syntheses of (-)-pentazocine and (-)-eptazocine through an aza-Prins cyclization.
Q. Chen (2012)
10.1021/JO034981K
A versatile indium trichloride mediated Prins-type reaction to unsaturated heterocycles.
A. Dobbs (2003)
10.1016/J.TETLET.2010.11.060
Triflic acid-promoted aza-Prins-Ritter reaction sequence: a novel synthesis of 4-amidopiperidine derivatives
B. Reddy (2011)
10.1016/J.TETLET.2010.04.093
Sc(OTf)3-catalyzed intramolecular aza-Prins cyclization for the synthesis of heterobicycles
B. Reddy (2010)
10.1021/jo500249c
Acid-mediated ring-expansion reaction of N-aryl-2-vinylazetidines: synthesis and unanticipated reactivity of tetrahydrobenzazocines.
Tomoaki Shimizu (2014)
10.1016/J.TETLET.2014.08.020
Naturally occurring scaffolds for compound library design: convenient access to bis-aryl 1-azaadamantanes carrying a vicinal amino alcohol motif
Abuzar Taheri (2014)
10.1016/J.TETLET.2010.01.059
An expeditious synthesis of 4-fluoropiperidines via aza-Prins cyclization
J. S. Yadav (2010)
10.1248/CPB.17.434
Syntheses of Azabenzobicycloalkanes
K. Mitsuhashi (1969)
10.1039/b915797b
A detailed investigation of the aza-Prins reaction.
A. Dobbs (2010)
10.1016/J.TET.2009.10.069
Synthesis of tetrahydropyrans and related heterocycles via prins cyclization; extension to aza-prins cyclization
C. Olier (2010)
10.1021/acs.joc.6b00725
Preparation of trans-2-Substituted-4-halopiperidines and cis-2-Substituted-4-halotetrahydropyrans via AlCl3-Catalyzed Prins Reaction.
G. Liu (2016)
10.1021/ja312065m
Total syntheses of lyconadins A-C.
T. Nishimura (2013)
10.1002/EJOC.201403607
A Cascade Aza‐Cope/Aza‐Prins Cyclization Leading to Piperidine Derivatives
Jothi L. Nallasivam (2015)
10.1021/acs.orglett.6b02072
Protecting-Group-Free Total Synthesis of (-)-Lycopodine via Phosphoric Acid Promoted Alkyne Aza-Prins Cyclization.
Donghui Ma (2016)
10.1021/jo101619d
Total synthesis of (+)-nankakurines A and B and (±)-5-epi-nankakurine A.
R. A. Altman (2010)
10.1002/HLCA.201000027
Trimethylsilyl Iodide‐Promoted Aza‐Prins Cyclization for the Synthesis of 4‐Iodopiperidines
G. Sabitha (2010)
10.1002/chem.201203415
Solvent-free, metal-free, aza-Prins cyclization: unprecedented access to δ-sultams.
Damien Clarisse (2013)
10.1021/ol3019924
Cycloaddition reaction of 2-vinylazetidines with benzyne: a facile access to 1-benzazocine derivatives.
T. Aoki (2012)
10.1021/acs.orglett.5b01919
Preparation of Fluorinated Tetrahydropyrans and Piperidines using a New Nucleophilic Fluorination Reagent DMPU/HF.
O. Okoromoba (2015)
10.1021/ol802362e
A new efficient catalytic system for the chemoselective cobalt-catalyzed cross-coupling of aryl Grignard reagents with primary and secondary alkyl bromides.
G. Cahiez (2009)
10.1016/J.TETLET.2009.12.007
A novel aza-Prins-Friedel-Crafts reaction for the synthesis of 4-arylpiperidines
J. S. Yadav (2010)
10.1055/S-0031-1289648
A Concise and DiastereoselectiveSynthesis of Piperidine and Indolizidine Alkaloids viaAza-Prins Cyclization
B. Reddy (2012)
10.2174/138527212800564196
Focused Update on the Prins Reaction and the Prins Cyclization
Isidro M. Pastor and Miguel Yus (2012)
10.1021/acs.joc.5b01301
Synthesis of Azabicycles via Cascade Aza-Prins Reactions: Accessing the Indolizidine and Quinolizidine Cores.
Freda K. I. Chio (2015)



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