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Current trends towards the synthesis of bioactive heterocycles and natural products using 1,3-dipolar cycloadditions (1,3-DC) with azomethine ylides
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Abstract In this revision a summary of the trends of the formation of complex or not so complex heterocyclic structures through 1,3-DC of azomethine ylides is described. Diastereo- and enantioselective processes as well as non-asymmetric cycloadditions constitute very important synthetic tools for achieving all these series of compounds. The contents are classified as follows: 1. Introduction 2. Synthesis of spiroxindoles 3. Synthesis of spiropyrrolidines 4. Synthesis of spiropiperidines and piperidines 5. Synthesis of pyrrolidines and fused pyrrolidines 6. Synthesis of pyrrolizidines and indolizidines 7. Synthesis of quinolone and isoquinolines 8. Conclusions
Biomimetic studies and biosynthetic theories strongly support
that general [3+2] cycloadditions1 take place frequently in
nature.2 In this line, azomethine ylides are useful synthetic
intermediates to access complex molecules, and in consequence,
their precursors are valuable building blocks in the elaboration
of structurally diverse biologically important heterocycles and
natural products. The main utility of these dipolar intermediates
is as component of 1,3-dipolar cycloaddition (1,3-DC) together
with electrophilic alkenes. Inter- and intramolecular versions of
these types of 1,3-DCs provide a potentially flexible and versatile
entry into the complex molecular framework with a pyrrolidine
core. These cycloadditions reach a special dimension when the
catalytic enantioselective process is successfully implemented. In
this way, up to four contiguous stereogenic centers can be
unambiguously generated in just one single step.
There are many excellent reports and reviews in the literature
about the generation, and applications concerning 1,3-DCs with
azomethine ylides but this field is in continuous expansion.3 In
this review the literature from 2015 through 2016 was covered
organizing the research in terms of biologically important
heterocycles and natural product from cascade 1,3-DC of
azomethine ylide to the most simple cycloaddition [the
application of this strategy to the generation of new materials or
polymers is not covered in this review].
2. Synthesis of spirooxindoles
Spirooxindole skeleton has an important biological role in
bioorganic and medicinal chemistry as well as in the drug
discovery programs.4 Synthesis of novel potentially bioactive
spirooxindoles has been reviewed in a recent paper and the work
related to spirooxindolepyrrolidines was also detailed.5
However, in this review some very recent publications have not
been highlighted. Therefore, in this revision the most recent work
regarding to spiroxindolepyrrolidines, obtained from a
multicomponent 1,3-dipolar cycloaddition (1,3-DC) of
azomethine ylides with the appropriate alkene, is reported.
The synthesis of spirooxindolepyrrolizidine derivatives 4 and 4’,
as well as their in vitro bioactivity against Mycobacterium
tuberculosis, were reported by Askri et al. Compounds 4 and 4’
were prepared from non-stabilized azomethine ylides, generated
in situ from isatin derivatives 2 and L-proline 1. Subsequent 1,3-
DC with (E,E)-1,3-bis(arylidene)indan-2-ones 3 yielded the
H. Ali Döndasa,*
María de Gracia Retamosab
José M. Sansanoc a Mersin University, Faculty of Pharmacy. Yenisehir Campus 33169 Yenisehir, Mersin (Turkey). b Instituto de Investigaciones Químicas (CSIC-US) and Centro de Innovación en Química Avanzada (ORFEO-CINQA) Avda. Américo Vespucio, 49,41092 Sevilla (Spain). c Departamento de Química Orgánica, Instituto de Síntesis Orgánica (ISO) and Centro de Innovación en Química Avanzada (ORFEO-CINQA), University of Alicante-03080 Alicante (Spain).
Scheme 77 Biologically important substituted pyrrolidines 270 ans 272 and alkaloid framework of natural product 274 via enantioselective 1,3-DC of azomethine ylides.
Tetrasubstituted endo-pyrrolidines 277 were prepared in the
presence of a metal catalyzed system (Ag2CO3/chiral amidphos
ligand 276). Imino esters 107 and dialkyl maleates 275 reacted
at room temperature in good yields. This multifunctional catalyst
was able to act in particular reactions with a Brönsted acid
domain (Scheme 78).117,118
Scheme 78 Enantioselective generation of endo-cycloadducts 277.
Chiral C-3 unsubstituted pyrrolidine cycloadducts 279 were
reported by Vicario and co-workers in the presence of L-proline
1 as catalyst with the idea of preparing deoxyazasugar
surrogates. The 1,3-DC was set up from diethyl
arylideneaminomalonates 171 and with acrolein 278 as
dipolarophile affording chiral cycloadducts, which were reduced
to the corresponding primary alcohols 279 in good yields and
high diastereo- and enantioselections (Scheme 79).119
These imino esters 171, derived from aminomalonates, and
ethynyl ketones were also employed by Deng and co-workers in
the enantioselective synthesis of chiral functionalised 2,5-
dihydropyrrole framework. In this example, the complex formed
by Cu(OAc)2·Ph-PhosFerrox 146 was the selected catalyst
affording cycloadducts in both high diastereoselectivities (98:2–
We thank Mersin University (Project no. BAP 2015-AP2-1342), and Universities of Seville and Alicante for their support. We also thank funding by the Spanish Ministerio de Ciencia e Innovación (MICINN) (Consolider INGENIO 2010 CSD2007-00006, CTQ2004-00808/BQU, CTQ2007-62771/BQU, CTQ2010-20387 and the Hispano-Brazilian project PHB2008-0037-PC), the Spanish Ministerio de Economía y Competitividad (MINECO) (projects CTQ2013-43446-P and CTQ2014-51912-REDC) FEDER, Generalitat Valenciana (PROMETEO/2009/039, and PROMETEOII/2014/017). M.G.R. thanks Junta de Andalucía (Grant 2012/FQM 1078 and a postdoctoral fellowship).
Biosketches
H.Ali Döndaş received his BSc. in 1990 from İnönü University, He received his MSc. in 1993 from Çukurova University and received his PhD degree in 1997 under the supervision of Professor Ronald Grigg (University of Leeds, UK) and received Best Ph.D Thesis award. In 1997 he was appointed Assistant Professor and become Associate Professor in 2001 at Mersin University. Since March 2007, he has been promoted to full Professor at Mersin University Faculty of Pharmacy, were he is currently the head of department at Basic Pharmaceutical Science. He has been working as Post-Doctoral Research Fellows (2000-2001) at University of Leeds (UK) with Professor Ronald Grigg and Post-Doctoral Research Fellows (2004) at University of Gent, Faculty of Bioscience Engineering Gent-Belgium with Professor Norbert De Kimpe. He has also been working as Visiting Researcher in 1998, Visiting Scholar in 2003 and 2005 at the University of Leeds, He was invited Visiting Research Scientist at the University of Leeds in 2008, 2015 and 2016.
Maria de Gracia Retamosa received her Ph.D. in 2008 at University of Alicante (Spain) under the guidance of Prof. Carmen Nájera and José Miguel Sansano. After that, she did several postdoctoral stays [Prof. Michael Greaneyat at the University of Edimburgh (UK, 2009), Prof. Jesús M. Sanz at the University Miguel Hernández (Elche, Spain, 2009–2011) and Prof. Fernando P. Cossío at the University of the Basque Country and Donostia International Physics Center (Spain, 2012–2016)]. Recently, she has joined to the group of Prof. Rosario Fernández and José M. Lassaletta as a postdoctoral researcher [CSIC (Sevilla, Spain)]. Her current research interests include asymmetric metal and organocatalysis and synthesis of compounds with pharmacological interest.
José Miguel Sansano was born in Rojales (Alicante), studied chemistry at the University of Alicante, where he obtained his B.Sc. and Ph.D. degrees in 1988 and 1994, respectively. His Thesis was supervised by Prof. C. Nájera and dealt about sulfone chemistry. After spending a two-year postdoctoral stay at the University of Leeds (U.K.) with Prof. R. Grigg, he joined the University of Alicante in 1996, where he was appointed Associate Professor in 2001. In 2010 he was promoted to Full Professor in the same University. He was invited visiting Professor at Chuo University in 2014. He is coauthor of more than 100 articles and he has supervised 10 PhD students.
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