Online citations, reference lists, and bibliographies.
Please confirm you are human
(Sign Up for free to never see this)
← Back to Search

Synthesis Of Multi-functionalized 1-azabicycles Through MAOS Acid Catalyzed Formal Aza-[3+3] Cycloaddition Of Heterocyclic Enaminones With Oxazolones

S. Cunha, Raimundo Francisco dos Santos Filho, Katharine Hodel Saraiva, Alene Vanessa Azevedo-Santos, D. Menezes
Published 2013 · Chemistry

Save to my Library
Download PDF
Analyze on Scholarcy
Share
Abstract This study describes the combination of microwave heating and green acid catalysis by Bi(NO 3 ) 3 ·5H 2 O and AcOH as a practical one-pot diastereoselective synthetic route to alkaloid-like multi-functionalized 3,4-disubstituted indolizidinones and quinolizidinones from cyclic enaminones and Erlenmeyer–Plochl azalactone derivatives, as an alternative methodology to access these synthetically and biologically important classes of structural scaffolds in a simple way. The potential biological activity of some synthesized alkaloid-like derivatives was tested against the human tumor lineage hepatoma (HepG-2), and their inhibitory effect evaluated after 24 and 48 h. The indolizidine-like scaffold appears to be crucial to biological activity in the investigated compounds.
This paper references
10.1016/S0040-4039(01)02067-6
Bismuth nitrate pentahydrate: a new and environmentally benign reagent for guanidylation of N-benzoylthioureas
S. Cunha (2002)
10.1002/JHET.5570410402
Recent development in preparation reactivity and biological activity of enaminoketones and enaminothiones and their utilization to prepare heterocyclic compounds
G. Negri (2004)
10.1021/JO0624290
A versatile strategy for divergent and diastereoselective synthesis of natural product-like polyhydroxylated indolizidines.
X. Jiang (2007)
10.1021/jm200608k
Targeting the prostaglandin F2α receptor for preventing preterm labor with azapeptide tocolytics.
C. Bourguet (2011)
10.2174/157017910791414490
Aza-[3 + 3] Annulations: A New Unified Strategy in Alkaloid Synthesis.
Grant S. Buchanan (2010)
10.1016/S0040-4020(02)01000-1
Applications of bismuth(III) compounds in organic synthesis
Nicholas M. Leonard (2002)
10.1055/S-2007-1000848
Reaction of Linear Push-Pull Enamines at the β′-Position
A. Kostyuk (2008)
10.1590/S0103-50532001000400006
Reaction of Diphenylcyclopropenone with N-Acylamidine Derivatives. Synthetic and Mechanistic Implications
S. Cunha (2001)
10.1016/S0040-4020(03)01201-8
Recent developments in the chemistry of enaminones
A. Elassar (2003)
10.1016/J.TETLET.2006.07.138
The first bismuth(III)-catalyzed guanylation of thioureas
Silvio Henriques Cunha (2006)
10.1055/S-2005-865295
Stereoselective synthesis of Aza- and diazabicyclo[X.Y.0]alkane dipeptide mimetics
W. Maison (2005)
10.1016/j.bmcl.2012.03.109
Synthesis of indolizidinone analogues of cytotoxic alkaloids: monocyclic precursors are also active.
A. Boto (2012)
10.1016/J.TET.2012.01.094
Synthesis of benzoindoloquinolizines via a Cu(I)-mediated C–N bond formation
Rattana Worayuthakarn (2012)
10.1016/J.BMC.2006.05.014
Oxazolones: new tyrosinase inhibitors; synthesis and their structure-activity relationships.
K. Khan (2006)
10.1351/pac199971060979
Enaminones: versatile intermediates for natural product synthesis
J. Michael (1999)
10.1016/J.TETLET.2003.10.125
Calcium acetate catalyzed synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones under solvent-free conditions
S. Paul (2004)
10.1590/S0103-50532009000400006
Guanylation of thiosemicarbazones: a new synthetic route to polysubstituted guanylhydrazones with antimicrobial activity
Silvio Cunha (2009)
10.1002/BSCB.19850941112
Étude de la Réactivité D'Ylideneoxazoline‐5‐Ones vis‐à‐Vis de Composés Enaminocarbonyles
A. Maquestiau (2010)
10.1016/J.TET.2005.08.052
The first synthesis of pyridinium N -benzoylguanidines by bismuth- and mercury-promoted guanylation of N -iminopyridinium ylide with thioureas
Silvio Henriques Cunha (2005)
10.1016/J.TET.2008.10.074
Iminium Ion Cascade Reactions: Stereoselective Synthesis of Quinolizidines and Indolizidines.
S. M. Amorde (2009)
10.1016/S0040-4020(02)00177-1
Unexpected ring size effect of the annulation reaction of heterocyclic secondary enamines with dicarboxylic acid dichlorides
Y. Cheng (2002)
10.1016/J.TETLET.2007.06.087
New alkaloid-like heterocycles via formal aza-[3+2] cycloaddition reaction of cyclic enaminones with cyclopropenones
S. Cunha (2007)
10.1248/CPB.33.2731
Studies on Amino Acid Derivatives. IV. Synthesis of 3-Amino-2 (1H)-pyridone Derivatives Using 4-Ethoxymethylene-2-phenyl-5-oxazolone
T. Chiba (1985)
10.1590/S0103-50532003000600012
The chemistry of enaminones, diazocarbonyls and small rings: our contribution
Concetta Kascheres (2003)
10.1039/c0cs00206b
Applications of bismuth(III) compounds in organic synthesis.
Jason M. Bothwell (2011)
10.1007/978-3-642-27239-4
Bismuth-Mediated Organic Reactions
Thierry Ollevier (2012)
10.1016/S0040-4020(00)01168-6
Study of N -benzoyl-activation in the HgCl 2 -promoted guanylation reaction of thioureas. Synthesis and structural analysis of N -benzoyl-guanidines
Silvio Henriques Cunha (2001)
10.2174/1385272043485936
Heterocyclic Enamines: The Versatile Intermediates in the Synthesis of Heterocyclic Compounds and Natural Products
Y. Cheng (2004)
10.1590/S0100-40422004000100019
Síntese de enaminonas
H. Ferraz (2004)
10.1002/0470024763
The chemistry of enamines
Z. Rappoport (1994)
10.1007/S00706-006-0577-Y
Synthesis and Structural Studies of 4-Thioxopyrimidines with Antimicrobial Activities
S. Cunha (2007)
10.1016/J.TETLET.2009.11.125
Catalyzing the Erlenmeyer Plöchl reaction: organic bases versus sodium acetate
Thomas P. Cleary (2010)
10.1016/J.TETLET.2012.09.125
Synthesis of α-aryl enaminones through reactions of β-aryl enones with benzyl azide
Silvio Henriques Cunha (2012)
10.1080/00397919708007288
Microwave-Mediated Domino Reactions in Dry Medium. Preparation of Dihydropyridinones and Pyridinones Structurally Related to Hantzsch Esters.
J. J. V. Eynde (1997)
10.1590/S0100-40422007000400035
Preparações e aplicações sintéticas recentes de enaminonas
H. M. Ferraz (2007)
10.1016/J.TET.2007.09.089
Aza- and Carbo-[3 + 3] Annulations of Exo-Cyclic Vinylogous Amides and Urethanes. Synthesis of Tetrahydroindolizidines and An Unexpected Formation of Hexahydroquinolines.
S. Ghosh (2008)
10.1021/ol2017438
Asymmetric aza-[3+3] annulation in the synthesis of indolizidines: an unexpected reversal of regiochemistry.
Grant S. Buchanan (2011)
10.1590/S0103-50532002000500014
The Michael Reaction of Enaminones with N-(p-tolyl)-maleimide: Synthesis and Structural Analysis of Succinimide-enaminones
Silvio Cunha (2002)
10.1021/OL062429M
Three distinct reactions of 3,4-dihydroisoquinolines with azlactones: novel synthesis of imidazoloisoquinolin-3-ones, benzo[a]quinolizin-4-ones, and benzo[d]azocin-4-ones.
Rattana Worayuthakarn (2006)
10.1021/cr800462w
More sustainable approaches for the synthesis of N-based heterocycles.
N. Candeias (2009)
10.1002/JLAC.197819780913
Dihydropyridine, V. Synthese von Aminodihydropyridonen
Horst Meyer (1978)
10.1055/S-2004-834801
Asymmetric Synthesis of Polyfunctionalized Pyrrolidines and Related Alkaloids
S. Pyne (2004)
10.1021/ar8000052
The practice of ring constraint in peptidomimetics using bicyclic and polycyclic amino acids.
S. Hanessian (2008)
10.1590/S0103-50532003000100017
Reaction of acyclic enaminones with methoxymethylene meldrum's acid: synthetic and structural implications
Silvio Cunha (2003)



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