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A Concise Domino Synthesis Of Benzo‐1,4‐heterocycle Compounds Via A Piancatelli/C–N Coupling/Michael Addition Process Promoted By La(OTf)3

J. Liu, Q. Shen, J. Yu, Mengyun Zhu, Jianwei Han, Limin Wang
Published 2012 · Chemistry

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A La(OTf)3-catalyzed domino method has been developed to synthesize the cis-1,4-benzoxazine derivatives from 2-furylcarbinols 1 and o-aminophenol derivatives, by a Piancatelli/C–N coupling/Michael addition process. A wide array of substrates could be used to give the desired products in good yields. Since this method involves simple reaction conditions and short reaction times, and has a broad substrate scope, it is particularly attractive for the efficient development of libraries of biologically relevant 1,4-benzoxazine derivatives. Furthermore, a similar strategy was also successfully applied to form 1,2,3,4-tetrahydroquinoxaline derivatives from 1 and N-substituted o-diaminobenzenes.
This paper references
10.1002/PRAC.18870350136
Ueber die Addition von Natriumacetessig‐ und Natriummalonsäureäthern zu den Aethern ungesättigter Säuren
A. Michael (1887)
10.1021/JO048329G
Improved heteroatom nucleophilic addition to electron-poor alkenes promoted by CeCl3.7H2O/NaI system supported on alumina in solvent-free conditions.
G. Bartoli (2005)
10.1016/J.TET.2011.09.004
Ytterbium pentafluorobenzoate as a novel fluorous Lewis acid catalyst in the synthesis of 2,4-disubstituted quinolines
J. Tang (2011)
10.1016/J.TETLET.2012.01.141
Yb(OTf)3-promoted effective benzylation and allylation with N-tosyl amino group as a stable leaving group
Jinqian Liu (2012)
10.3987/COM-08-11606
A New and Facile Synthesis of Rutaecarpine Alkaloids
C. Lee (2009)
10.1021/OL0712475
Enantiopure 1,4-benzoxazines via 1,2-cyclic sulfamidates. Synthesis of levofloxacin.
John F Bower (2007)
10.1016/J.JFLUCHEM.2009.01.002
One-pot synthesis of quinoline-4-carboxylic acid derivatives in water: Ytterbium perfluorooctanoate catalyzed Doebner reaction
Limin Wang (2009)
10.1055/S-2004-837210
Rare Earth Perfluorooctanoate [RE(PFO)3]-Catalyzed Condensations of Indole with Carbonyl Compounds
Limin Wang (2005)
10.1002/JHET.5570220143
Synthesis of 2-(2-imidazolinyl) substituted 2,3-dihydro-4H-1,4-benzothiazine and 3,4-dihydro-2H-1,4-benzoxazines
R. C. Butler (1985)
10.1021/JM00079A016
Conformationally restrained analogues of pravadoline: nanomolar potent, enantioselective, (aminoalkyl)indole agonists of the cannabinoid receptor.
T. D'ambra (1992)
10.1016/J.BMC.2004.07.048
Discovery of a new class of potent, selective, and orally active prostaglandin D2 receptor antagonists.
K. Torisu (2004)
10.1021/JM970795T
New substituted 1,4-benzoxazine derivatives with potential intracellular calcium activity.
A. Bourlot (1998)
10.1021/JO01171A001
Attempts to find new antimalarials; amino alcohols derived from 1,2,3,4-tetrahydrophenanthrene.
E. May (1946)
10.3987/COM-08-11629
Regiospecific synthesis of unsubstituted basic skeletons of heterocycles containing nitrogen neighboring an aromatic ring by the reductive ring expansion reaction using diisobutylaluminum hydride
Hidetsura Cho (2009)
10.1021/OL050125E
Ytterbium triflate-promoted tandem one-pot oxidation-Cannizzaro reaction of aryl methyl ketones.
M. Curini (2005)
10.1002/ADSC.200404211
One‐Pot Synthesis of cis‐Isoquinolonic Acid Derivatives via Three‐Component Reaction of Homophthalic Anhydride with Aldehydes and Amines using Ytterbium(III) Triflate as Catalyst
Limin Wang (2005)
10.1016/J.TETLET.2006.04.121
Ytterbium triflate catalyzed synthesis of β-keto enol ethers
M. Curini (2006)
10.1002/EJOC.200801115
Preparation of Triaryl-and Triheteroarylmethanes under Ytterbium Triflate Catalysis and Solvent-Free Conditions
S. Genovese (2009)
10.1055/S-1997-1290
THE SYNTHESIS OF REDUCED PHENOXAZINES AS POTENTIAL CHAIN-BREAKING ANTIOXIDANTS
D. Brown (1997)
10.1016/J.TETLET.2010.09.015
Ytterbium triflate catalyzed synthesis of chlorinated lactones
S. Genovese (2010)
10.1248/CPB.44.756
Design and synthesis of 6-chloro-3,4-dihydro-4-methyl-2H-1,4-benzoxazine-8-carboxamide derivatives as potent serotonin-3 (5-HT3) receptor antagonists.
T. Kuroita (1996)
10.1039/B709337N
Mild lanthanide(III) catalyzed formation of 4,5-diaminocyclopent-2-enones from 2-furaldehyde and secondary amines: a domino condensation/ring-opening/electrocyclization process.
Sze-Wan Li (2007)
10.1021/ol9003299
Highly efficient copper-catalyzed domino ring opening and Goldberg coupling cyclization for the synthesis of 3,4-dihydro-2H-1,4-benzoxazines.
R. K. Rao (2009)
10.1016/J.TET.2004.11.079
Facile Yb(OTf)3 promoted one-pot synthesis of polyhydroquinoline derivatives through Hantzsch reaction
Limin Wang (2005)
10.1021/OL062344L
Cobalt-catalyzed aryl-sulfur bond formation.
Y. Wong (2006)
10.1002/ANGE.201006633
Titelbild: Light‐Driven Transport of a Molecular Walker in Either Direction along a Molecular Track (Angew. Chem. 1/2011)
M. J. Barrell (2011)
10.1021/JM00163A061
6-Benzoxazinylpyridazin-3-ones: potent, long-acting positive inotrope and peripheral vasodilator agents.
D. Combs (1990)
10.1016/J.JFLUCHEM.2010.12.002
A facile synthesis of α-aminophosphonates catalyzed by ytterbium perfluorooctanoate under solvent-free conditions
J. Tang (2011)
10.1055/S-0029-1219350
Solvent-Free Anti-MarkovnikovAddition of Thiols to Alkenes Using Anhydrous Cerium(III)Chloride as Catalyst
C. Silveira (2010)
10.3987/COM-09-11700
(S)-MANDELATE-MEDIATED DYNAMIC KINETIC RESOLUTION OF α-BROMO ESTERS FOR ASYMMETRIC SYNTHESES OF AMINOFLAVONES, DIHYDROQUINOXALINONES AND DIHYDROBENZOXAZINONES
Y. M. Lee (2009)
10.1248/CPB.44.103
Novel potassium channel activators: synthesis and structure-activity relationship studies of 3,4-dihydro-2H-1,4-benzoxazine derivatives.
Y. Matsumoto (1996)
10.2174/138527205774913105
Editorial [Hot Topic: Special Issue on Organophosphorus Chemistry (Guest Editor: Gyorgy Keglevich)]
György Keglevich (2007)
10.1021/IE020702S
Straightforward Synthesis of 2-Substituted 3,4-Dihydro-2H-1,4-benzoxazines under Solid−Liquid Phase Transfer Catalysis Conditions
D. Albanese (2003)
10.1016/S0040-4039(00)71357-8
A useful preparation of 4-substituted 5-hydroxy-3-oxocyclopentene
G. Piancatelli (1976)
10.1016/0040-4020(95)98693-C
Novel 1,4-benzoxazine derivatives of pharmacological interest. Electrochemical and chemical syntheses
M. Largeron (1995)
10.1021/JO0602221
Facile N-arylation of amines and sulfonamides and o-arylation of phenols and arenecarboxylic acids.
Z. Liu (2006)
10.1016/J.TETLET.2010.11.128
Ytterbium triflate catalyzed synthesis of β-functionalized indole derivatives
F. Epifano (2011)
10.1016/S0040-4020(01)85949-4
Reactions of some conjugated dienes with an o-quinone monoimide
H. W. Heine (1988)
10.1021/jo102506x
CuI-nanoparticles-catalyzed selective synthesis of phenols, anilines, and thiophenols from aryl halides in aqueous solution.
H. Xu (2011)
10.1016/J.TETLET.2007.02.064
“Ytterbium triflate catalyzed synthesis of β-enaminones”,
F. Epifano (2007)
10.1021/jo101619d
Total synthesis of (+)-nankakurines A and B and (±)-5-epi-nankakurine A.
R. A. Altman (2010)
10.1021/OL0477935
Copper-catalyzed synthesis of vinyl sulfides.
C. Bates (2004)
10.1016/S0968-0896(99)00049-8
Novel vasopressin V2 receptor-selective antagonists, pyrrolo[2,1-a]quinoxaline and pyrrolo[2,1-c][1,4]benzodiazepine derivatives.
Y. Ohtake (1999)
10.1016/J.TETLET.2011.07.108
Efficient trans-acetoacylation mediated by ytterbium(III) triflate as a catalyst under solvent-free condition
G. B. Rao (2011)



This paper is referenced by
10.3390/molecules181012290
The Piancatelli Rearrangement: New Applications for an Intriguing Reaction
C. Piutti (2013)
10.1002/CHIN.201318161
A Concise Domino Synthesis of Benzo-1,4-heterocycle Compounds via a Piancatelli/C—N Coupling/Michael Addition Process Promoted by La(OTf)3.
Jinqian Liu (2013)
10.3762/bjoc.15.160
Enantioselective PCCP Brønsted acid-catalyzed aza-Piancatelli rearrangement
Gabrielle R Hammersley (2019)
10.1021/jo402331t
Scandium pentafluorobenzoate-catalyzed unexpected cascade reaction of 2-aminobenzaldehydes with primary amines: a process for the preparation of ring-fused aminals.
D. Mao (2013)
10.1002/EJOC.201700957
Brønsted Acid Catalyzed Domino Aza‐Piancatelli Rearrangement/Michael Reaction: Construction of 1,4‐Benzodiazepin‐5‐ones in One Pot
Kiranmai Nayani (2017)
10.1002/chem.201603592
Harnessing the Lewis Acidity of HFIP through its Cooperation with a Calcium(II) Salt: Application to the Aza-Piancatelli Reaction.
D. Lebœuf (2016)
10.1016/J.TET.2014.05.085
Design of C2-symmetric salen ligands and their Co(II)- or Yb(III)-complexes, and their role in the reversal of enantioselectivity in the asymmetric Henry reaction
Shengying Wu (2014)
10.1039/c3cc49191a
ZnCl2-catalyzed chemoselective cascade reactions of enaminones with 2-furylcarbinols: a versatile process for the synthesis of cyclopenta[b]pyrrole derivatives.
C. Wang (2014)
10.1039/c4cc01196a
The versatility of furfuryl alcohols and furanoxonium ions in synthesis.
Matthew J Palframan (2014)
10.1039/c5ob00944h
Cascade rearrangement of furylcarbinols with hydroxylamines: practical access to densely functionalized cyclopentane derivatives.
Gesine K. Veits (2015)
10.1039/c5ob01616a
Sequential aza-Piancatelli rearrangement/Friedel-Crafts alkylation for the synthesis of pyrrolo[1,2-d]benzodiazepine derivatives.
B. Reddy (2016)
10.1002/EJOC.201403580
Furan's Gambit: Electrophile‐Attack‐Triggered Sacrifice of Furan Rings for the Intramolecular Construction of Azaheterocycles
I. V. Trushkov (2015)
10.1039/d0sc00542h
A chiral cobalt(II) complex catalyzed enantioselective aza-Piancatelli rearrangement/Diels–Alder cascade reaction
B. Shen (2020)
10.1016/J.TETLET.2017.02.068
One-pot synthesis of tricyclo-1,4-benzoxazines via visible-light photoredox catalysis in continuous flow
Guolin Wu (2017)
10.1002/anie.201607714
Catalytic Enantioselective Aza-Piancatelli Rearrangement.
H. Li (2016)
10.1021/acs.joc.5b00056
Chemoenzymatic asymmetric synthesis of 1,4-benzoxazine derivatives: application in the synthesis of a levofloxacin precursor.
M. López-Iglesias (2015)
10.1021/acs.joc.7b00090
Catalyst-Controlled Chemodivergent Modification of Indoles with 2-Furylcarbinols: Piancatelli Reaction vs Cross-Dehydrative Coupling Reaction.
Jianfeng Xu (2017)
10.1039/c4ob02220c
A Sc(OTf)3-catalyzed cascade reaction of o-aminoacetophenone with methanamine: construction of dibenzo[b,h][1,6]naphthyridine derivatives.
D. Mao (2015)
10.1002/chem.201705851
Synthesis and Applications of Stenhouse Salts and Derivatives.
Rafael F A Gomes (2018)
10.1021/ol5032987
Calcium(II)-catalyzed aza-Piancatelli reaction.
D. Lebœuf (2014)
10.1002/EJOC.201400073
Lewis‐Acid‐Catalyzed Benzylic Reactions of 2‐Methylazaarenes with Aldehydes
D. Mao (2014)
10.1002/EJOC.201301762
Synthesis of Indoles by Domino Reaction of 2-(Tosylamino)benzyl Alcohols with Furfurylamines: Two Opposite Reactivity Modes of the α-Carbon of the Furan Ring in One Process
Maxim G. Uchuskin (2014)
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