| Current
Organic Chemistry
ISSN: 1385-2728
Current Organic Chemistry
Volume 12, Number 9, June 2008
Contents
Heterocyclic Chemistry
Guest Editor: Jan Bergman
Editorial Pp. 690
Synthetic Applications of the Nenitzescu Reaction
to Biologically Active 5-Hydroxyindoles Pp. 691-717
Shivaputra A. Patil, Renukadevi Patil and
Duane D. Miller
[Abstract]
Building Bicyclic Polyhydroxylated Alkaloids: An Overview
from 1995 to the Present Pp. 718-750
M.D. López, J. Cobo and M. Nogueras
[Abstract]
The Imino-Pinacol Coupling Reaction Pp.
751-773
Vanessa Faugeroux and Yves Génisson
[Abstract]
Development and Application of Effective Protocols
for the Synthesis of Arylheterorenes and Biheteroarils, Including
Bioactive Derivatives, by Highly Regioselective Transition
Metal Catalyzed Direct Intermolecular Arylation Reactions
of Five Membered Heteroarenes with (Hetero)aryl Halides
Pp. 774-790
Fabio Bellina, Silvia Cauteruccio and Renzo
Rossi
[Abstract]
Abstracts
[Back to top]
Editorial
The Nenitzescu reaction is a classical methodology
to quickly obtain highly functionalized indole derivatives.
The reaction is now brought up-to-date by Drs Patil, Patil
and Miller from the University of Tennessee, Memphis, USA.
Bicyclic polyhydroxylated alkaloids constitutes an interesting
and biologically active class of molecules. Stereochemical
challenges are multipresent. All these aspects are attended
by Prof. López and her co-workers from the University
of Jaén, Spain.
The imino-pinacol coupling offers an attractive access to
1,2-diamines, which in turn have important applications in
medicinal chemistry and asymmetric catalysis. This field is
now reviewed by Prof. Génisson and Dr Faugeroux from
Université Paul Sabatier, Toulouse, France.
The final contribution authored by Prof. R. Rossi and his
co-workers from the University of Pisa, Italy, features recent
denvelopment of arylheteroarenes and biheteroaryls.
Jan Bergman
Karolinska Institute
Novum
Huddinge, Sweden
[Back to top]
Synthetic Applications of the Nenitzescu Reaction to Biologically
Active 5-Hydroxyindoles
Shivaputra A. Patil, Renukadevi Patil and
Duane D. Miller
A variety of natural and unnatural molecules containing
a 5 hydroxyindole moiety have displayed strong pharmacological
activities. In this context the Nenitzescu reaction has proven
to be extremely useful for the preparation of 5-hydroxyindoles
directly from simple and accessible materials like 1,4-benzoquinone
and enamines. This review will summarize recent applications
for the synthesis of complex 5-hydroxyindole derivatives such
as pyrimido[4,5-b]indol-4 amines, 5H-benzo[b]carbazoles, 5’-hydroxynaltrindolomorphinans,
and 3-[3-(amidomethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-5
yloxy]propylphosphonic acid (LY311727) which possess important
biological activities. The Mechanism of the Nenitzescu reaction
is discussed and as is recent utilization of solid phase chemistry
to the Nenitzescu reaction.
[Back to top]
Building Bicyclic Polyhydroxylated Alkaloids: An Overview
from 1995 to the Present
M.D. López, J. Cobo and M. Nogueras
This review deals with the latest developments in the
synthesis of bicyclic iminosugars.
[Back to top]
The Imino-Pinacol Coupling Reaction
Vanessa Faugeroux and Yves Génisson
interest in imino-pinacol coupling arises from the access
it offers to 1,2-diamines, a highly valuable class of compounds
that have found constant applications in medicinal chemistry
and asymmetric catalysis. The present paper intends to cover,
from the 60’s to present, the different chemical approaches
applied to the imino-pinacol coupling, setting each procedure
in an historical perspective and delineating general reactivity
trends. This review shows that, even though the last 40 years
has witnessed an impressive evolution, there is still room
for improvement both in terms of flexibility and stereoselectivity.
[Back to top]
Development and Application of Effective Protocols
for the Synthesis of Arylheterorenes and Biheteroarils, Including
Bioactive Derivatives, by Highly Regioselective Transition
Metal Catalyzed Direct Intermolecular Arylation Reactions
of Five Membered Heteroarenes with (Hetero)aryl Halides
Fabio Bellina, Silvia Cauteruccio and Renzo
Rossi
The past decade has witnessed significant progress in
highly regioselective direct arylation of azoles with aryl
halides. This account aims to summarize recent progress in
the development and application of these reactions. In particular,
it describes and comments on the results obtained in the development
of efficient protocols for the selective Pdcatalyzed direct
C-5 arylation of 1-aryl-1H-imidazoles, 1-benzyl-1H-imidazole
and 1-methyl-1H-imidazole and the highly regioselective
Pdcatalyzed and Cu-mediated direct C-2 arylation of azoles,
including free (NH)-imidazole, -benzimidazole and -indole.
The utility of these novel protocols for the concise and efficient
preparation of 1,5-diaryl- and 1,2-diaryl-1H-imidazoles,
including derivatives of potential pharmacological interest,
4(5)-aryl-, 4,5-diaryl- and 4,5-diaryl-1-methyl-1H-imidazoles,
2-arylbenzothiazoles and 2-arylbenzimidazoles, including bioactive
compounds or their precursors, and 2,4(5)-diaryl-1H-imidazoles
is also disclosed. Finally, this account illustrates the results
of an attempt to optimize a protocol for the direct C-2 arylation
of 1H-indole, which enabled the development of a
new, convenient and functional group-tolerant version of the
Ullmann reaction for the Cu-mediated highly regioselective
N-arylation of 1H-indole derivatives and
9H-carbazole.
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