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Six-Membered Hetarenes with One Nitrogen or Phosphorus Atom. Science of Synthesis Vol. 1. Edited by D. St. C

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Six-Membered Hetarenes with
One Nitrogen or Phosphorus Atom
Science of Synthesis, Vol. 1. Edited by
D. St. C. Black.
Georg Thieme
Verlag, Stuttgart
2005. 1320 pp.,
E 2000.00.—ISBN
This book is Volume 15 of 48 volumes of
the new Houben–Weyl collection Science of Synthesis. This collection, which
will be completed in the next few years,
is divided into six categories. More
information on the whole series and
some opinions of reviewers can be found
on the web site Volume 15
belongs to Category 2 (Volumes 9–17),
which is devoted to hetarenes, and
covers the synthesis of heterocyclic
compounds. The major part concerns
methods for the synthesis of pyridines
and their derivatives (pyridine 1-oxide,
pyridinium salts) as well as pyridinones,
quinolines and quinolinones, isoquinolines and isoquinolinones, naphthyridines, acridines, and phenanthridines.
The aim of this part (1096 pp.) is to
present the state of the art concerning
the synthesis of this venerable class of
compounds, so important in synthetic
and medicinal chemistry. A much
shorter part (93 pp.) concerns the more
recent and less developed class of hetarenes with one P atom and is intended to
help future research in this particular
field, visibly still in its infancy.
The Houben–Weyl series, since its
beginning (almost one century!), conAngew. Chem. Int. Ed. 2006, 45, 3399 – 3400
stitutes a well-known series of textbooks
on organic synthesis. Originally the
ambition was to cover, as far as possible,
all aspects of organic synthesis. In doing
so, it effectively became a sort of bible in
the field; but times have now changed!
The enormous amount of literature now
available defies such a task, which is
now increasingly assumed by databases
such as Beilstein or SciFinder. These
databases are of incomparable value
when one wants to find a rather welldefined product or reaction. However, if
one wants general approaches for the
synthesis of species such as pyridines,
one will be faced with hundreds of
thousands of results and a prohibitive
quantity of work to analyze them. Thus,
there is a need for comprehensive
reviews covering such topics of broad
interest. This is the laudable goal of the
series Science of Synthesis.
The chapter classification of synthetic methods for a particular class of
molecules follows the traditional
Houben–Weyl numbering system. It is,
in my opinion, a valuable classification,
but quite difficult to comprehend. It is
indeed difficult to understand where
you are when, opening a page, you are
faced with a paragraph number such as! Nevertheless, as compensation for that, it has the great
advantage of introducing a logical
system into a very complex situation,
such as the analysis of all methods now
available for the synthesis of pyridines.
The presentation of the different
approaches to the synthesis of compound subclasses of nitrogen and phosphorus six-membered heterocycles is
first divided into several categories,
such as ring-closure reactions, ring transformations, substituent modifications,
etc. Under these categories are then
approaches and, for each one, different
methods and their variations. A typical
experimental procedure is always
described at the end. The examples
illustrating a strategy are not necessarily
the most relevant, but they are always
well chosen for a good understanding.
For example, methods for the syntheses
of pyridines and pyridinium salts, which
are very similar, have been separated,
whereas they could have been joined
together. Examples in chiral series are
also rare or absent. I particularly appre-
ciated the classification used for ringclosure reactions. In the case of the
synthesis of pyridines, for example, the
classification is based on the number of
C C and C N bonds formed, followed
by the number and nature of fragments
used. This is particularly important in
view of the complex situation in this
field, which generally uses empirical
parameters (reaction name, type of
reagent or reaction, etc.). This is also
very useful for evaluating the merits of a
particular approach, for example with
regard to its convergence or its possible
use in multicomponent approaches.
This Volume 15 of Science of Synthesis is of considerable value for anyone
involved in the synthesis of the class of
substances covered. I received this
volume when I was trying to evaluate
new results concerning pyridine synthesis. The task was turning out to be very
difficult, because of scattered data and a
lack of comprehensive and up-to-date
literature. This book was exactly what I
needed for this purpose, and I think that
the authors are to be thanked for their
large contribution of high-quality work.
Christian Marazano
Institut de Chimie des Substances
Gif-sur-Yvette (France)
DOI: 10.1002/anie.200585380
The Organic Chemistry of Sugars
Edited by Daniel E.
Levy and Pter
Fgedi. CRC Press/
Taylor & Francis,
Boca Raton 2006.
928 pp., hardcover
$ 199.95.—ISBN
Compared with many other organic
molecules, the special quality of carbohydrates, which are known to play a key
role in many biological processes, is
their high density of functional groups
and their impact on each other. As a
6 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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synthesis, one, atom, nitrogen, membered, hetarenes, edited, six, vol, phosphorus, science
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