Online citations, reference lists, and bibliographies.
← Back to Search

Metal-free, One-pot Conversion Of Proline Derivatives Into 2-aryl-3-iodo Pyrrolidines By A Sequential Scission-iodination-arylation Process.

Venkateswara Rao Batchu, Iván Romero-Estudillo, A. Boto, J. Miguélez
Published 2014 · Chemistry, Medicine

Cite This
Download PDF
Analyze on Scholarcy
Share
The metal-free, direct conversion of readily available proline derivatives into 2-aryl-3-iodopyrrolidines is carried out under mild conditions and in good yields, using a sequential radical decarboxylation-oxidation-iodination-arylation reaction. These iodinated pyrrolidines are valuable precursors of other compounds. For instance, they can be cyclized to tricyclic compounds or undergo dehalogenation to 2-aryl-2,5-dihydro-1H-pyrroles, which are iminosugar and 2-arylpyrrole precursors. This process provides a short pathway to a variety of alkaloid and drug analogues of potential pharmaceutical interest.
This paper references
10.1021/ja104305s
Pyrrole synthesis via allylic sp3 C-H activation of enamines followed by intermolecular coupling with unactivated alkynes.
S. Rakshit (2010)
10.1021/OL050897A
A Re(V)-catalyzed C-N bond-forming route to human lipoxygenase inhibitors.
Rachana V Ohri (2005)
10.1016/J.TETLET.2009.09.004
Synthesis of substituted 3-iodopyrroles by electrophilic cyclization of propargylic aziridines
M. Yoshida (2009)
10.1021/ol303159h
Ruthenium-catalyzed pyrrole synthesis via oxidative annulation of enamides and alkynes.
B. Li (2013)
10.1016/J.TETLET.2009.04.082
Enantiopure alkaloid analogues and iminosugars from proline derivatives: stereocontrol in sequential processes
A. Boto (2009)
10.1021/CR078199M
Lamellarins and related pyrrole-derived alkaloids from marine organisms.
H. Fan (2008)
10.1002/anie.200903743
Total synthesis of pentabromo- and pentachloropseudilin, and synthetic analogues--allosteric inhibitors of myosin ATPase.
R. Martin (2009)
10.1002/EJOC.200901320
Recent Developments in the Synthesis of Pyrrolidine‐Containing Iminosugars
Bridget L. Stocker (2010)
10.1039/c1cc11363a
A straightforward one-pot multicomponent synthesis of polysubstituted pyrroles.
Xufeng Lin (2011)
10.1021/jo8012989
Short, stereoselective synthesis of the naturally occurring pyrrolidine radicamine B and a formal synthesis of nectrisine.
C. Ribes (2008)
10.1021/ol201173a
One-pot stereoselective synthesis of 1,2-amino alcohol derivatives.
A. Boto (2011)
10.1021/jo702385n
Novel one-pot, three-component synthesis of new 2-alkyl-5-aryl-(1H)-pyrrole-4-ol in water.
B. Khalili (2008)
10.1039/A904578C
Synthesis of aromatic heterocycles
T. Gilchrist (1998)
10.1039/b815195d
A facile synthesis of pyrrolo-(di)-benzazocinones via an intramolecular N-acyliminium ion cyclisation.
F. King (2009)
10.1021/ol301552c
Synthesis of α,γ-peptide hybrids by selective conversion of glutamic acid units.
Carlos J Saavedra (2012)
10.1021/ol301676z
"Customizable" units in di- and tripeptides: selective conversion into substituted dehydroamino acids.
Carlos J Saavedra (2012)
10.1002/EJOC.201000997
One-Pot Conversion of Proline Derivatives into Iodinated Iminosugar-Based Nucleosides, Useful Precursors of Highly Functionalized Nucleoside Analogues
A. Boto (2010)
10.1002/EJOC.201200685
A Stereoselective Route to Aza-C-aryl Glycosides from Arynes and Chiral Nitrones
Rama Kanwar Khangarot (2012)
10.1016/J.TETLET.2012.01.086
Synthesis Of Pentabromopseudilin And Other Arylpyrrole Derivatives Via Heck Arylations
C. Schwalm (2012)
10.1039/c0cc04372a
Gold-catalysed rearrangement of O-vinyl oximes for the synthesis of highly substituted pyrroles.
Simbarashe Ngwerume (2011)
10.1039/C2CC32510A
Gold(i)-catalyzed cyclization of 2-(1-alkynyl)-alk-2-en-1-one oximes: a facile access to highly substituted N-alkoxypyrroles.
Mei Zhang (2012)
10.1021/JA074330W
A new use of Wittig-type reagents as 1,3-dipolar cycloaddition precursors and in pyrrole synthesis.
Daniel J St Cyr (2007)
10.1021/jo9004487
Catalytic, one-pot synthesis of beta-amino acids from alpha-amino acids. Preparation of alpha,beta-peptide derivatives.
Carlos J Saavedra (2009)
10.1039/c4cc00493k
Pyrroles versus cyclic nitrones: catalyst-controlled divergent cyclization of N-(2-perfluoroalkyl-3-alkynyl) hydroxylamines.
Qin Zeng (2014)
10.1016/J.TET.2010.05.055
A new method for the synthesis of 3-aryl-6-(2-pyrrolyl)pyridazines
C. Song (2010)
10.1021/OL302270Z
2,4- vs 3,4-disubsituted pyrrole synthesis switched by copper and nickel catalysts.
Feng Chen (2012)
10.1016/J.TET.2014.01.037
An atom-economic synthesis of functionalized pyrroles via a sequential metal-catalyzed three-component reaction
Li Yu-feng (2014)
10.1002/EJOC.201301731
Nucleoside Analogues: Synthesis and Biological Properties of Azanucleoside Derivatives
D. Hernández (2014)
10.1039/b815227f
A one-pot oxidative decarboxylation-Friedel-Crafts reaction of acyclic alpha-amino acid derivatives activated by the combination of iodobenzene diacetate/iodine and iron dust.
Renhua Fan (2008)
10.1002/anie.201006367
Formal syntheses of (-)- and (+)-phalarine.
H. Ding (2011)
10.1021/ol102075y
Horner-Wadsworth-Emmons reagents as azomethine ylide analogues: pyrrole synthesis via (3 + 2) cycloaddition.
M. Morin (2010)
10.1016/J.TET.2012.03.045
Ring-closing iodoamination of homoallylic amines for the synthesis of polysubstituted pyrrolidines: application to the asymmetric synthesis of (−)-codonopsinine
S. Davies (2012)
10.1021/ja804021m
Bis-sulfonyl ethylene as masked acetylene equivalent in catalytic asymmetric [3 + 2] cycloaddition of azomethine ylides.
A. López-Pérez (2008)
10.1039/c1cc11300c
Tambjamine alkaloids and related synthetic analogs: efficient transmembrane anion transporters.
Paulina Iglesias Hernández (2012)
10.1016/J.TET.2011.01.020
1,3-Dipolar cycloaddition approach to pyrrolidine analogues of C-nucleosides related to pseudouridine
E. Coutouli-Argyropoulou (2011)
10.1016/J.TET.2009.10.030
Regioselective halogenation of aminopyrimidinyl-pyrrole carboxylic acid derivatives
E. Vanotti (2009)
10.1002/EJOC.201100312
Palladium-Catalyzed Direct Arylations of Five-Membered Heteroarenes Bearing N-Monoalkylcarboxamide Substituents
Nouria Laidaoui (2011)
10.1016/j.bmc.2012.04.014
Discovery, synthesis, and biological evaluation of novel pyrrole derivatives as highly selective potassium-competitive acid blockers.
Haruyuki Nishida (2012)
10.1016/J.BMCL.2006.11.059
1,5-Biaryl pyrrole derivatives as EP1 receptor antagonists. Structure-activity relationships of 6-substituted and 5,6-disubstituted benzoic acid derivatives.
A. Hall (2007)
ピロール保護 | 文献情報 | J-GLOBAL 科学技術総合リンクセンター
Jolicoeur Benoit (2006)
10.1039/b917644f
Multicomponent reactions for the synthesis of pyrroles.
V. Estévez (2010)
10.1002/EJOC.201001611
Betti Reaction of Cyclic Imines with Naphthols and Phenols – Preparation of New Derivatives of Betti's Bases
C. Cimarelli (2011)
Reviews on anion
S. Fukuzumi (2011)
10.1002/EJOC.201101274
One‐Pot Conversion of Serine Derivatives and Amino Sugars into Oxazine Derivatives of γ‐Aryl‐γ‐(hydroxy)amines
A. Boto (2012)
2491–2515. 2 (a) For some bioactive alkaloids: Lamellarins
Int. Ed (2001)
10.1021/jo301031t
Stereoselective conversion of sugar derivatives into C-nucleosides.
J. Miguélez (2012)
10.1016/J.TETLET.2013.04.014
Three-component direct synthesis of substituted pyrroles from easily accessible chemical moieties using hypervalent iodine reagent
Nikhil C. Jadhav (2013)
10.1021/jo402181w
Modular synthesis of lamellarins via regioselective assembly of 3,4,5-differentially arylated pyrrole-2-carboxylates.
Masashi Komatsubara (2014)
10.1016/J.TET.2004.05.008
Synthesis of pyrrolo[3,2-b]benzofurans and pyrrolo[3,2-b]naphthofurans via addition of a silyloxypyrrole to activated quinones
M. Brimble (2004)
10.1002/EJOC.200901055
A New Method for the Synthesis of Multisubstituted Pyrroles of Biological Interest by Double Nucleophilic Addition to α,β‐Unsaturated Imines
A. Takahashi (2010)
10.1039/c2ob06659a
Olefin cross-metathesis for the synthesis of heteroaromatic compounds.
T. Donohoe (2012)
10.1021/ol400062w
A new pyrrole synthesis via silver(I)-catalyzed cycloaddition of vinylogous diazoester and nitrile.
Roland Billedeau (2013)
10.1021/JO071155T
Synthesis of unnatural amino acids from serine derivatives by beta-fragmentation of primary alkoxyl radicals.
A. Boto (2007)
10.1039/c3cc44896g
An efficient synthesis of polysubstituted pyrroles via copper-catalyzed coupling of oxime acetates with dialkyl acetylenedicarboxylates under aerobic conditions.
X. Tang (2013)
10.1039/c1cc12061a
Transmembrane anion transport by synthetic systems.
Cally J. E. Haynes (2011)
10.1039/c3cs60015g
Recent advances in the synthesis of pyrroles by multicomponent reactions.
V. Estévez (2014)
10.1021/JA072577N
Ruthenium catalyzed decarbonylative arylation at sp3 carbon centers in pyrrolidine and piperidine heterocycles.
D. Gribkov (2007)
10.1016/J.TETLET.2011.05.044
Site-selective Suzuki–Miyaura reactions of 2,3,5-tribromo-N-methylpyrrole
Serge-Mithérand Tengho Toguem (2011)
10.1021/ol100838m
Iron-mediated direct Suzuki-Miyaura reaction: a new method for the ortho-arylation of pyrrole and pyridine.
Jun Wen (2010)
10.1039/c2cc38099d
Three-component access to pyrroles promoted by the CAN-silver nitrate system under high-speed vibration milling conditions: a generalization of the Hantzsch pyrrole synthesis.
Verónica Estévez (2013)
10.1039/c1cc10751h
One-pot nitro-Mannich/hydroamination cascades for the direct synthesis of 2,5-disubstituted pyrroles using base and gold catalysis.
D. Barber (2011)
10.1039/b913066g
1,3-Dipolar cycloadditions: applications to the synthesis of antiviral agents.
C. Nájera (2009)
10.1016/j.bmc.2008.10.063
Synthesis and biological evaluation of a 2-aryl polyhydroxylated pyrrolidine alkaloid-based library.
En-Lun Tsou (2008)
10.1039/A900689C
Convenient synthesis of C -aza-2,3-dideoxynucleosides
A. Momotake (1999)
10.1021/ol303224e
Versatile pyrrole synthesis through ruthenium(II)-catalyzed alkene C-H bond functionalization on enamines.
L. Wang (2013)
10.1021/OL070412D
Short and efficient synthesis of chiral furyl carbinols from carbohydrates.
A. Boto (2007)
10.1021/ol4006129
A highly diastereoselective and enantioselective synthesis of polysubstituted pyrrolidines via an organocatalytic dynamic kinetic resolution cascade.
T. Cheng (2013)
10.1002/anie.201300477
Aerobic synthesis of pyrroles and dihydropyrroles from imines: palladium(II)-catalyzed intramolecular C-H dehydrogenative cyclization.
Zhuangzhi Shi (2013)
10.1039/c3cc43682a
Oxidative cross-coupling/cyclization to build polysubstituted pyrroles from terminal alkynes and β-enamino esters.
J. Ke (2013)
10.1002/anie.200805122
The copper-catalyzed decarboxylative coupling of the sp3-hybridized carbon atoms of alpha-amino acids.
Hai-Peng Bi (2009)
10.1016/J.TETLET.2006.07.120
Total synthesis of (−)-radicamine B
M. K. Gurjar (2006)
10.1021/jo2011347
Enantioselective, palladium-catalyzed α-arylation of N-Boc pyrrolidine: in situ react IR spectroscopic monitoring, scope, and synthetic applications.
G. Barker (2011)
10.1039/b900236g
Creative approaches towards the synthesis of 2,5-dihydro- furans, thiophenes, and pyrroles. One method does not fit all!
Matthew Brichacek (2009)
10.1021/jo1011448
Synthesis of highly substituted pyrroles via nucleophilic catalysis.
Simbarashe Ngwerume (2010)
10.1021/ol902142w
Microwave-assisted synthesis of 2'-O-aryluridine derivatives.
Yusuke Oeda (2009)
10.1039/c2cc30490b
Facile synthesis of 2-alkyl/aryloxy-2H-azirines and their application in the synthesis of pyrroles.
X. Qi (2012)
10.1039/c1cc10779h
Novel dipolarophiles and dipoles in the metal-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine ylides.
J. Adrio (2011)
10.1016/J.TET.2006.08.071
Tetrahedron report number 776Pyrrole protection
Benoît Jolicoeur (2006)
10.1039/B002063J
Stereoselective synthesis of C-4′-aminouridines (uracil C-4-amino-D-ribonucleosides)
M. Yokoyama (2000)
10.1021/jo800478a
Efficient conversion of carbohydrates into 1-C-alditols: application to the synthesis of chiral gamma-substituted butenolides and bicyclic alkaloid analogues.
A. Boto (2008)
10.1016/J.BMC.2004.11.018
Antimycobacterial compounds. Optimization of the BM 212 structure, the lead compound for a new pyrrole derivative class.
M. Biava (2005)
10.1002/CHIN.201201250
Indoles and Indolizidines in Natural Product Synthesis
Sarah M Bronner (2012)
10.1039/c3cc43844a
"One pot" regiospecific synthesis of polysubstituted pyrroles from benzylamines and ynones under metal free conditions.
Jinhai Shen (2013)
10.1016/J.BMCL.2006.08.111
Genotoxic activity of halogenated phenylglycine derivatives.
A. Boto (2006)
10.1039/c2cc35759c
Recent progress in research on anion-responsive pyrrole-based π-conjugated acyclic molecules.
H. Maeda (2013)
10.1021/JO035744K
Imino-C-nucleoside synthesis: heteroaryl lithium carbanion additions to a carbohydrate cyclic imine and nitrone.
G. B. Evans (2004)
10.1021/OL0609210
Radicamines A and B: synthesis and revision of the absolute configuration.
C. Yu (2006)
10.1021/ol402305b
A novel tandem sequence to pyrrole syntheses by 5-endo-dig cyclization of 1,3-enynes with amines.
G. Bharathiraja (2013)
10.1039/c3cc49683j
Synthesis of multi-substituted pyrroles using enamides and alkynes catalyzed by Pd(OAc)2 with molecular oxygen as an oxidant.
Y. Xu (2014)
10.1002/ANIE.200300582
Chemistry and biology of roseophilin and the prodigiosin alkaloids: a survey of the last 2500 years.
A. Fürstner (2003)
10.1039/c3ob41269e
A one-pot coupling-addition-cyclocondensation sequence (CACS) to 2-substituted 3-acylpyrroles initiated by a copper-free alkynylation.
Jan Nordmann (2013)
10.1016/S0040-4039(99)00151-3
HECK REACTION OF ENDOCYCLIC ENECARBAMATES WITH DIAZONIUM SALTS. FORMAL ENANTIOSELECTIVE SYNTHESES OF ALKALOIDS (-)-CODONOPSINE AND (-)-CODONOPSININE, AND THE SYNTHESIS OF A NEW C-ARYL AZASUGAR
D. F. Oliveira (1999)
10.1039/b926045e
Chiral molecules containing the pyrrole framework.
S. Thirumalairajan (2010)
10.1039/c2cc32848h
Supramolecular electron transfer by anion binding.
S. Fukuzumi (2012)
10.1039/c2ob25407g
Flow synthesis using gaseous ammonia in a Teflon AF-2400 tube-in-tube reactor: Paal-Knorr pyrrole formation and gas concentration measurement by inline flow titration.
Philippa B. Cranwell (2012)
2491–2515. 2 (a) For some bioactive alkaloids: Lamellarins
Int. Ed (2001)
10.1016/J.TET.2007.05.032
Peripheral aryl-substituted pyrrole fluorophores for glassy blue-light-emitting diodes
Wen-Jang Kuo (2007)
10.1016/S0040-4039(00)02343-1
Stereoselective synthesis of azanucleosides aza-stavudine (aza-D4T), aza-2′,3′-didehydro-3′-deoxyuridine (aza-D4U), and its hydrogenated analogues from an endocyclic enecarbamate
E. R. Costenaro (2001)
10.1021/JO015877A
Synthesis of 2,3-disubstituted pyrrolidines and piperidines via one-pot oxidative decarboxylation-beta-iodination of amino acids.
A. Boto (2001)
10.1039/B605245M
Biological formation of pyrroles: nature's logic and enzymatic machinery.
C. Walsh (2006)
10.1021/jo300892u
Conformation and chiral effects in α,β,α-tripeptides.
Carlos J Saavedra (2012)
10.1039/A802247J
Synthesis and properties of C-aza-2-deoxy-L-lyxonucleosides†
M. Yokoyama (1998)



This paper is referenced by
Semantic Scholar Logo Some data provided by SemanticScholar