Aneta KOACZEK*, Iwona FUSIARZ, Justyna AWECKA, Danuta BRANOWSKA Institute of

Chemistry, Siedlce University, Siedlce, Poland

Please cite as: CHEMIK 2014, 68, 7, 620628

Introduction
Sulfonamides (sulfa drugs) were the first drugs largely employed
and systematically used as preventive and chemotherapeutic agents
against various diseases [1]. Over 30 drugs containing this functionality
are in clinical use, including antihypertensive agent bosentan [2],
antibacterial [3], antiprotozoal [4], antifungal [5], antiinflammatory
[6], nonpeptidic vasopressin receptor antagonists [7] and translation
initiation inhibitors [8]. Some important sulfonamide derivatives
used as carbonic anhydrase inhibitors of commercial importance
[9]. They are also effective for the treatment of urinary, intestine,
and ophthalmic infections, scalds, ulcerative colitis [10], rheumatoid
arthritis [11], male erectile dysfunction as the phosphodiesterase-5
inhibitor sildenafil better known under its commercial name,
Viagra [12], and obesity [13]. More recently, sulfonamides are used
as an anticancer agent [14], as the antiviral HIV protease inhibitor
amprenavir [15] and in Alzheimers disease [16].

Sulfonamides via sulfonyl chloride from thiols

Due to the broad applicability of sulfonamides, it is desirable to find
general and effective methods for their synthesis. Thus synthesis of
these compounds is of continuing interest. To date many synthetic
methods have been reported. Some of the most common and recent
methods are illustrated briefly below and are provide via sulfonyl
chloride or using transition metals as catalyst or Grignard reagents.
The sulfonylation of amines with chlorides in the presence of a base
is the most typical method for preparing of sulfonamides. This method
involves the nucleophilic attack by ammonia, primary or secondary
amines, with sulfonyl chlorides in the presence of a base. Although this
method is efficient, it requires the availability of sulfonyl chloride, some
of which are difficult to store or handle. In turn, sulfonyl chlorides can
be prepared from the corresponding thiols using a number of methods,
commonly by bubbling Cl2 gas into aqueous acid or a biphasic mixture
containing the thiol. Sulfonyl chlorides are prepared also by treating
sulfonic acids with chlorinating agents such as SOCl2 [23], POCl3 [24]
or PCl5 [25]. Recently, the direct oxidative conversion of thiols into
sulfonamides with H2O2-SOCl2 (Fig. 2) was reported by Bahrami et al.
[26] where upon acts with amines, the corresponding sulfonamides
were obtained in excellent yields in very short reaction times [27].

Fig. 1. The general structure of sulfonamides,

if R=R1=H is sulfanilamide

Sulfonamides are compounds, which have a general structure

represented by Figure1. After sulfanilamide discovery, thousands of
chemical variations were studied and the best therapeutic results
were obtained from the compounds in which one hydrogen atom of
the SO2NH2 group was replaced by heterocyclic ring [17]. To date
more than twenty thousand sulfanilamide derivatives have been
synthesized. These syntheses have resulted in the discovery of new
compounds with varying pharmacological properties in this main
structure, R, R1 may be hydrogen, alkyl, aryl or hetero aryl etc.
The lipophilicity of the N1 group has the largest effect on protein
binding, and generally, the more lipids soluble a sulfonamide is the
more of it will be protein bound [18]. The aniline (N4) amino group
is very important for activity because any modification of it other
than to make prodrugs results in a loss of activity [19]. Moreover
sulfonamides are also inactive if p-amino group is acylated, benzene
is substituted, sulfonamide group not attached directly to benzene
ring. More advanced studies revealed that modified sulfonamides
showing high to moderate antibacterial activity [20]. Aliphatic
sulfonamides have highest powerful antibacterial activity for Gram
(-) bacteria than Gram (+) and antibacterial activity decreases as the
length of the carbon chain increases [21]. Also, novel macrocyclic
bis-sulfonamides showed antimicrobial activities [22].

Corresponding author:
Aneta KOACZEK, M.Sc., Eng. e-mail: aneta-kolaczek@wp.pl

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Fig. 2. Conversion of thiols into sulfonamides with H2O2-SOCl2

Mentioned above methodology was optimized as a combinatorial

library (parallel format). Sulfonamides were smoothly prepared in good
to high yields when aryl thiols carrying either electron-donating or
electron-withdrawing substituents [28]. Recently modification of this
standard method concerns the using N-chlorosuccinimide (NCS) and
tetrabutylammonium chloride-water system in acetonitrile delivered
sulfonyl chloride in situ. Furthermore, authors have developed a onepot process for preparing sulfonyl azides from thiols under these
conditions in the presence of NaN3. This convenient one-pot synthesis
of sulfonyl azides from sulfonic acids was reported by Jong et al. [29].
The advantages are excellent yields, the cheapness and availability of
the reagents, easy and clean workup, extremely fast reaction, high
chemoselectivity (Fig. 3).

Fig. 3. Method concerns the using N-chlorosuccinimide (NCS)

and t-Bu4NCl

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Biological activity and synthesis of sulfonamide

derivatives: a brief review

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A method of formation of sulfonamides from thiols was reported

by Wright et al. [30], requiring in situ synthesis of a sulfonyl chloride
using sodium hypochlorite (commercial bleach) mediated oxidation
of thiol. This methodology introduces several advantages, such as
readily availability of the reagents as well as controlled amount
of the oxidant used. The resulting sulfonyl chlorides were then
trapped with benzylamine in the subsequent reaction to produce
sulfonamides up to 98% yield (Fig. 4).

Fig. 4. Sodium hypochlorite as mediated oxidation of thiols

Trichlorocyanuric acid (TCCA) and benzyltrimethyl ammonium

chloride in water were used to generate a controlled amount of
chlorine into aprotic solvent (MeCN). The use by Bonk et al. [31] of
TCCA introduces the advantage of high-purity chlorine production
compare to that of hypochlorite. The research group modified this
methodology by adding the subsequent amine into a one-pot reaction,
generating sulfonyl chloride in situ, and furnishing sulfonamides under
1 hour (Fig. 5).

Moreover Barrett et al. [35] reported the reaction of sulphur

dioxide with various organometallic reagents to give sulfinic acid salts,
which can be directly treated with sulfuryl chloride and amine to furnish
sulfonamides in good yields. Modification of this method was used
by Woolven et al. [36] where the bench-stable colorless solid chargetransfer complex generated from the combination of DABCO and
sulfur dioxide, DABSO, can replace gaseous SO2 in organic synthesis.
Reactions with Grignard reagents form sulfinates, which can then be
converted in situ to sulfonamides (Fig. 8).

Fig. 8. Synthesis of sulfonamide with using organometallic reagents

Sulfonamides from sulfenamides

Another innovative example of sulfonamides synthesis was
illustrated in the synthesis of 2-amino-9H-purin-6-sulfonamide. Mild
and selective oxidants have been used by Revankar et al. [37]. They
reported the oxidation of 2-amino-9H-purin-6-sulfenamide using one
equivalent of m-CPBA in 48% yield (Fig. 9). More amounts of m-CPBA
(4eq) delivered target compound with slightly better 53% yield.

Fig. 9. Oxidation of sulfenamides with using m-CPBA

Fig. 5. Synthesis of sulfonamides via reaction with trichlorocyanuric
acid (TCCA)

Sulfonamides from sulfonic acid

Sulfonyl chloride occurs as intermediate starting from sulfonic acid.
As an easy and handy, this synthesis is performed under microwave
irradiation, and has shown a good functional group tolerance, and is
high yielding [32] (Fig. 6).

Sulfonamides via using transition metal catalyst

Transition metal catalyzed cross-coupling CN bond formation
has been studied extensively, where the most well-known, palladium
catalyzed N-arylation is the Buchwald-Hartwig reaction [38]. Up
to now catalysts base on a few transition metals have been examined
for the N-arylation of sulfonamides. The first one is Pd. For example
a biaryl phosphine ligand, t-BuXPhos and K3PO4 in tert-amyl alcohol
was found to be the optimal base-solvent combination for a Pdcatalyzed sulfonamidation of aryl nonafluorobutanesulfonates. The
reaction conditions were tolerant of various functional groups.
The only identified limitation of this methodology is the inability
of 2,6-disubstituted aryl nonaflates to efficiently participate in the
reaction [39] (Fig. 10).

Fig. 6. Synthesis of sulfonamides with using microwave irradiation

This reaction was also performed in classical heating delivered

corresponding sulfonamide in good to excellent yields [33].
Chavasir et al. [34] reported the novel using of trichloroacetonitriletriphenylphosphine complex (Cl3CCN/PPh3) for sulfonamide
construction. It was found that the optimal yield is reached when 3:3:1
(Cl3CCN:PPh3:sulfonic acid) ratio and dichloromethane are used,
however the yields are not reproducible in other solvents and ratios.
One of the notable advantages of this methodology is that it is not limited
to aromatic sulfonyl chlorides, and can be applied to heterocyclic and
aliphatic sulfonyl chlorides (Fig. 7).

A convenient, general, and high yielding Pd-catalyzed crosscoupling of methanesulfonamide with aryl bromides and chlorides
eliminates concern over genotoxic impurities that can arise when
aniline is reacted with methanesulfonyl chloride [40] (Fig. 11).

Fig. 7. Method performed with trichloroacetonitriletriphenylphosphine complex

Fig. 11. Pd-catalyzed cross-coupling

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Fig. 10. Pd-catalyzed sulfonamidation

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Microwave heating enables a Borrowing Hydrogen strategy

to form C-N bonds from alcohols and amines, removes the
need for solvent and reduces the reaction times, while the
results are comparable with those using thermal heating [41]
(Fig. 12). Activation of this process demands the presence of
ruthenium catalyst.

Fig. 16. Copper-catalyzed oxidative coupling

A facile and efficient indium-catalyzed sulfonylation of amines allows

the synthesis of a wide range of sulfonamides in excellent yields. The
method showed a generality for substrates including less nucleophilic
and sterically hindered anilines, and it is also applicable for preparing
sulfonic esters from sulfonyl chlorides and alcohols [46] (Fig. 17).
Fig. 12. Borrowing Hydrogen strategy in C-N bonds formation

A Rh(II)-catalyzed oxidative coupling of aldehydes and sulfonamides

provides N-sulfonylcarboxamides in one step. Various sulfonamides
were found to react with aromatic and aliphatic aldehydes to afford
the desired products in very good yields [42] (Fig. 13).
Fig. 17. Indium-catalyzed sulfonylation

Fig. 13. Rh(II)-catalyzed oxidative coupling

The second metal, used more often, is Cu. It is more likely to be

used for large scale synthesis. An effective method for N-arylation
on sulfonamide using 0.1 equivalent of copper(II) acetate in air
and arylboronic acid to get N-arylsulfonamide near-quantitative
yield [43] (Fig. 14).

Fig. 14. N-arylation on sulfonamide with boronic acid derivatives

More recently, Guo et al. [44] have synthesized a range of

sulfonamides using copper (I) catalysed coupling and aryl bromide/
iodide (Fig. 15). During the optimization process, they found that
using an amino acid as a ligand introduces several advantages such
as easy removal after the reaction. After screening several amino
acids, they found that N-methylglycine and N,N-dimethylglycine are
the most effective with Cu(I). Together with K3PO4 as base, and DMF
as the solvent, all desired N-arylsulfonamides can be generated in up
to 99% yield.

Fig. 15. N-arylsulfonamides via Cu(I) using

Lately a new and convenient method for the construction of

sulfonamides via copper-catalyzed oxidative coupling between sodium
sulfinates and amines with 1 atm O2 or DMSO as the oxidant was
described. This method provides efficient and robust synthesis of
functional sulfonamides in good yields and excellent chemoselectivity.
Several various amines and sulfinates salt were tested. The detailed
mechanistic studies showed that this transformation may go through
a single electron transfer (SET) pathway [45] (Fig. 16).

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Conclusions
In summary, the synthesis of sulfonamide derivatives has been
reported in many ways. These classes of compounds are considered
as scalffolds in medicinal chemistry to drug development with
different biological activities. In organic chemistry, these compounds
have a functional application in the industry in some products of
health, food colorants and others, therefore it is necessary to continue
with research projects that help to synthesize new compounds with
sulfonamide group.
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*Aneta KOACZEK, M.Sc., Eng. is a graduate of Siedlce University (2013).
She actively participated in an academic movement of students. She is a coauthor of 3 conference presentations.
e-mail: aneta-kolaczek@wp.pl

Iwona FUSIARZ, M.Sc., Eng. is a graduate of Siedlce University (2013). She

is a co-author of 1 conference presentations.
e-mail: iwus89@wp.pl

Justyna AWECKA, Ph.D., Eng. graduated from the Faculty of Mathematics

and Chemistry at the University of Podlasie in Siedlce (present Siedlce
University of Natural Sciences and Humanities) in 2004. She obtained her
Ph.D. degree in the Faculty of Natural Sciences at the Siedlce University of
Natural Sciences and Humanities (2011). She is the stipendiary of Minister of
National Education and Sport. Nowadays, she is working at the Department
of Chemistry UPH in Siedlce. Her scientific interests are: heterocyclic
compounds and organic sulfur compounds. She is the co-author of 11 articles,
2 application patents and 18 papers and posters presented at national and
international conferences.
e-mail: laweckaj@uph.edu.pl

Danuta BRANOWSKA, D.Sc., Eng. graduated from the Chemistry Institute

of the Higher School of Agriculture and Pedagogy in Siedlce in 1989. In 1999
she received the Ph.D. at the Faculty of Pharmacy Pozna University of Medical
Science. She did her habilitation at the Silesian University of Technology in
Gliwice in 2008. She is currently working as an associate Professor at Siedlce
University of Natural Sciences and Humanities. Research interests: organic
chemistry, synthesis of heteroaromatic compounds, photoluminescence
compounds, modern metaloorganic reactions. She is the author of 35 scientific
papers, 7 Polish patents and 2 patent applications as well as about 40 papers
and posters presented at national and international conferences.
e-mail: danuta.branowska@uph.edu.pl

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