Ecofriendly solventless synthesis and reduction reaction of some triazole compounds and evaluation of their antimicrobial activity

DOI: 10.1080/00397911.2011.632831

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Synthetic Communications p. 1328 - 1336 (2013)

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Authors:

Oezil, Musa

Mentese, Emre

Karaoglu, Senguel Alpay

Kahveci, Bahittin

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Article abstract of DOI:10.1080/00397911.2011.632831

A number of triazole-3-one compounds have been synthesized, and reduction of the carbonyl group in the molecule has been carried out to give a corresponding hydroxyl group that possesses asymmetric carbon atom in good yields and short reaction times. It is ecofriendly because it is produced by straightforward microwave irradiation in the absence of solvent. All newly synthesized compounds were also screened for their antimicrobial activities. The antimicrobial activity study revealed that 2d, 2i, 3c, and 3g-j showed good activity against a variety of microorganisms. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

Full text of DOI:10.1080/00397911.2011.632831

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Ecofriendly Solventless Synthesis and

Reduction Reaction of Some Triazole

Compounds and Evaluation of Their

Antimicrobial Activity

Musa Özil ^a, Emre Menteşe ^a, Şengül Alpay Karaoğlu ^b& Bahittin

Kahveci ^c

^aDepartment of Chemistry, Faculty of Sciences and Arts, Recep

Tayyip Erdoğan University, Rize, Turkey

^bDepartment of Biology, Faculty of Sciences and Arts, Recep Tayyip

Erdoğan University, Rize, Turkey

^cDepartment of Nutrition and Dietetics, Faculty of Health Sciences,

Karadeniz Technical University, Trabzon, Turkey

Version of record first published: 21 Feb 2013.

To cite this article: Musa Özil , Emre Menteşe , Şengül Alpay Karaoğlu & Bahittin Kahveci (2013):

Ecofriendly Solventless Synthesis and Reduction Reaction of Some Triazole Compounds and Evaluation

of Their Antimicrobial Activity, Synthetic Communications: An International Journal for Rapid

Communication of Synthetic Organic Chemistry, 43:9, 1328-1336

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Synthetic Communications¹, 43: 1328–1336, 2013

ISSN: 0039-7911 print=1532-2432 online

DOI: 10.1080/00397911.2011.632831

ECOFRIENDLY SOLVENTLESS SYNTHESIS AND

REDUCTION REACTION OF SOME TRIAZOLE

COMPOUNDS AND EVALUATION OF THEIR

ANTIMICROBIAL ACTIVITY

Musa Ozil, Emre Mentes¸e, S¸engu¨l Alpay Karaoglu, and

Bahittin Kahveci³

¹Department of Chemistry, Faculty of Sciences and Arts, Recep Tayyip

Erdog˘an University, Rize, Turkey

²Department of Biology, Faculty of Sciences and Arts, Recep Tayyip

Erdog˘an University, Rize, Turkey

³Department of Nutrition and Dietetics, Faculty of Health Sciences,

Karadeniz Technical University, Trabzon, Turkey

GRAPHICAL ABSTRACT

Abstract A number of triazole-3-one compounds have been synthesized, and reduction of the

carbonyl group in the molecule has been carried out to give a corresponding hydroxyl group

that possesses asymmetric carbon atom in good yields and short reaction times. It is eco-

friendly because it is produced by straightforward microwave irradiation in the absence

of solvent. All newly synthesized compounds were also screened for their antimicrobial

Received October 2, 2011.

Address correspondence to Musa Ozil, Department of Chemistry, Faculty of Sciences and Arts,

Recep Tayyip Erdog˘an University, Rize 53100, Turkey. E-mail: musa.ozil@rize.edu.tr

1328

SYNTHESIS AND REDUCTION OF TRIAZOLES

1329

activities. The antimicrobial activity study revealed that 2d, 2i, 3c, and 3g–j showed good

activity against a variety of microorganisms.

Supplemental materials are available for this article. Go to the publisher’s online edition

of Synthetic Communications¹to view the free supplemental ﬁle.

Keywords Antimicrobial activity; green chemistry; microwave-assisted synthesis;

solvent-free; 1,2,4-triazole-3-one

INTRODUCTION

A dramatic increase in antibiotic resistance, especially among Gram-positive

bacteria, triggered a clear need for the discovery of new antimicrobials rather than

analogs of the existing ones.^[1]Traditionally, small molecules have been a reliable

source for discovering novel biologically active compounds.

1,2,4-Triazole compounds have been found to be useful for applications in

medicine and agriculture.^[2]The synthesis, reactions, and biological properties of

substituted triazole constitute a signiﬁcant part of modern heterocyclic chemistry.^[3]

Compounds with the triazole ring system have many pharmacological properties and

play important roles in biochemical processes. There have been reported applications

in a wide spectrum of potential biological properties, such as antifungal,^[4]antitu-

mor,^[5]analgesic,^[6]antibacterial,^[7,8]and cancer therapy.^[9]Antibacterial activity data

of these structures showed considerable activity against Gram-negative and

Gram-positive bacteria as well as some strains of fungi.^[10–12]Thus, the heterocyclic

system is an attractive scaffold to be utilized for exploiting chemical diversity.

The application of microwave (MW) irradiation as an effective energy source for

activation of reactions has now become a very popular and useful technology in

organic chemistry.^[13]Nowadays economical and environmental conditions are forcing

the chemical community to search for more efﬁcient ways of performing chemical

transformations in a single operation by reusing catalysts and avoiding toxic and costly

reagents, large amounts of solvents, and expensive puriﬁcation techniques.^[14]Reac-

tions using solid-supported reagents and scavengers have created considerable interest

among synthetic chemists around the world.^[15]Because of several advantages in terms

of yield, purity, and selectivity, supported reagents have been used under solvent-free

conditions for the synthesis of various important synthetic intermediates.^[16]

The combination of microwave irradiation and solvent-free reaction conditions

leads to enhanced reaction rates, greater yields of pure products, easier workup, and

selective conversions, all advantages of the ecofriendly approach.^[17,18]Consequently,

this protocol should be welcomed in these environmentally conscious times.

The growing importance of triazole compounds has led to the development of

new methods for their synthesis, including microwave-assisted synthesis. Thus, the

development of simple, convenient, safe, and efﬁcient methods for the preparation

of these molecules still continues to be an interesting and attractive area of research

in synthetic chemistry.

In the present work, we studied the triazole formation, taking different para-

meters of solid supports like (i) montmorillonite KSF, (ii) montmorillonite K10,

(iii) alumina, and (iv) silica gel. However, no reaction occurred. Encouraged by

recent focus on the green chemical theme of eliminating the use of solvents, we

M. OZIL ET AL.

1330

extended our studies to neat reactions, those that could be made successful without

any solid supports. It did not lead to any side reactions and no detectable by-product

was observed. Consequently, we extended this condition to the synthesis of com-

pounds (2a–j).

RESULTS AND DISCUSSION

Recently, we reported the synthesis of triazole compounds by both microwave

irradiation and conventional heating.^[19,20]However, poor reaction yields, selectivity,

and long reaction times dissuade more systematic study of the reaction. Therefore,

we planned to focus our study on the synthesis and reduction of triazole compounds

via conventional and microwave-assisted synthesis under solvent-free media.

(N⁰-Ethoxycarbonyl)-4-alkyl(aryl)hydrazonic acid ethyl ester can be considered

as useful intermediate leading to the formation of heterocycles, such as 1,2,4-

triazole-3-ones. We synthesized some (N⁰-ethoxycarbonyl)-4-alkyl(aryl)hydrazonic

acid ethyl ester (1a–j) according to the literature.^[20–22]

At ﬁrst, we had to optimize the reaction conditions for the synthesis of

5-aryl(alkyl)-4-(4-benzoylphenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (2a–j) by the

reaction of (N⁰-ethoxycarbonyl)-4-alkyl(aryl)hydrazonic acid ethyl ester (1a–j) with

p-aminobenzophenone. We tried different reaction conditions to carry out this reac-

tion under microwave irradiation in the absence of solvent. For this we used solid

support, such as montmorillonite KSF, montmorillonite K10, alumina, and silica

gel, but no reaction occurred. However, reaction occurred when heated neat above

the melting points under microwave irradiation (Scheme 1).

The polarity of the system is increased during the reaction progress from the

neutral ground state (GS) to the dipolar transition state (TS) for cyclization. Conse-

quently, microwave stabilizing effects by dipole–dipole interactions with the electric

Scheme 1. Pathway for the formation of the 3H-1,2,4-triazol-3-ones.

SYNTHESIS AND REDUCTION OF TRIAZOLES

1331

ﬁeld are increased with the polarity of reactants. Such an explanation of microwave

effects is supported by calculations suggesting a relation between microwave

irradiation and the polarity of the transition state,^[23]so we can say that in our reac-

tions speciﬁc microwave effects occur when the reaction mixture is melting.

Encouraged by these ﬁndings, we next investigated the optimum reaction con-

dition for the synthesis of 3H-1,2,4-triazol-3-ones (2a–j) under conventional conditions

and a monomodal microwave oven. For conventional conditions, the reaction

occurred in an oil bath for 5 h at 170 ^ꢀC. For a Discover monomodal microwave oven,

mixture was irradiated in closed vessels with pressure control at 150^ꢀC for 3 min (hold

time) at 300W maximum power.

By comparision of data, it is obvious that the microwave irradiation protocol

resulted in much faster reactions and signiﬁcantly greater yields (Table 1) than the

thermal heating process.

Here, we report our further investigations concerning the reduction of the car-

bonyl group in the molecule, which have been carried out to produce a corresponding

hydroxyl group that possesses asymmetric carbon atoms under microwave irradiation

as well as conventional methods. However, there was no reduction of carbonyl in the

triazole ring but only a reduction of carbonyl in the substitute group bounding the

N-4 nitrogen atom. Thus, in a conventional experiment, we obtained reductive pro-

ducts 3a–j in the presence of an ion exchange solid (Amberlyst-15 H^þ) in the aprotic

solvent tetrahydrofuran (THF). Amberlyst-15 (H^þ) is an effective material for

reduction of hindered and unreactive ketones.^[24]However, we obtained 3a–j in the

presence of alumina under microwave irradiation in the absence of solvent (Scheme 2).

Varma and Saini^[25]demonstrated the reduction of the carbonyl group in a

solid state under microwave irradiation. Here, we synthesized 3a–j in a monomode

microwave synthesizer for 2 min at 300 W maximum power with high yield (Table 2).

A comparison of the spectral data gave some information as to the nature of

the products. In this context, a comparison of the infrared (IR) spectral data clearly

indicates the formation of compounds 3a–j by the disappearance of the C O band at

Table 1. Comparison of yields under microwave irradiation and conven-

tional heating (for compounds 2a–j)

Yield (%)

Compound

Oil bath^a

Microwave^b

^a5 h at 170 ^ꢀC.

^b3 min at 150 ^ꢀC.

M. OZIL ET AL.

1332

Scheme 2. Pathway for the reduction reaction of the carbonyl group.

about 1649–1668 cm^ꢁ1in compounds 2a–j and the appearance of the OH band at

about 3375–3439 cm^ꢁ1and C—O band at about 1013–1059 cm^ꢁ1in compounds

3a–j. In addition, in the H NMR spectrum of 3a–j revealed for OH group doublet

signals at about 5.91–6.08 ppm in the dimethylsulfoxide (DMSO-d₆) and broad

singlet signal at about 2.88–3.38 ppm in the CDCl₃and revealed for CH group doub-

let signals at about 5.70–5.77 ppm in the DMSO-d₆and singlet signals at about

5.80–5.86 ppm in the CDCl₃. The ¹³C NMR spectrum of 3a–j shows a signal that

indicates the appearance of CH groups at about 73.52–75.81 ppm and the disappear-

ance of the C O group at about 194.84–195.69 ppm in compounds 2a–j.

Antibacterial Activities

While antibacterial, antituberculotic, and antifungal activity were shown on

some tested compounds, some of compounds did not show any antimicrobial

Table 2. Comparison of yields under microwave irradiation and conven-

tional heating (for compounds 3a–j)

Yield (%)

Compound

THF^a

Microwave^b

^a12 h at rt.

^b2 min at 150 ^ꢀC.

SYNTHESIS AND REDUCTION OF TRIAZOLES

1333

Table 3. Antimicrobial activity of the compounds (mg=ml)

Microorganism and minimal inhibition concentration

Compound

—

>128

—

250

—

31.3

—

125

—

31.3

—

15.6

—

125

—

125

—

62.5

—

125

—

62.5

125

250

62.5

125

250

62.5

125

250

31.3

15,6

62,5

62.5

Amp.

Strep.

Flu.

Notes. Ec, E. coli ATCC 25922; Yp, Y. pseudotuberculosis ATCC 911; Pa, P. aeruginosa ATCC 43288;

Sa, S. aureus ATCC 25923; Ef, E. faecalis ATCC 29212; Bc, B. cereus 702 Roma; Ms, M. smegmatis

ATCC607; Ca, C. albicans ATCC 60193; S. cerevisiae RSKK 251; Amp., ampicillin; Strep., streptomycin;

Flu., ﬂuconazole; —, no activity.

activity. Compounds 2i, 3c, 3g–3j demonstrated antitubercolitic activity (M. smeg-

matis) in 15.6–250 mg=ml concentration. Compound 2d exhibited antimicrobial

activity against only yeast (C. albicans, S. cerevisiae) fungals. Compounds 3c and

3g–3j exhibited antimicrobial activity against Gram-positive M. smegmatis in

15–250 mg=ml concentration. The results are shown in Table 3.

CONCLUSION

We have developed a novel and efﬁcient approach for the synthesis of some

3H-1,2,4-triazol-3-ones and reduction of carbonyl group in these molecules under

microwave irradiation in the absence of solvent. The important advantages of this

procedure include (a) operational simplicity (ease of setup and workup), (b) safe

and environmentally benign solvent-free procedure (eliminating toxic organic

solvents as reaction medium), (c) good yield of the products with high purity, (d)

mild reaction conditions, (e) good selectivity, (f) general applicability, accommodat-

ing a variety of substitution patterns, and (g) effective antibacterial activities

(Table 3) for the compounds 3a–j.^[26]

M. OZIL ET AL.

1334

EXPERIMENTAL

Chemistry

Melting points were determined in open capillaries on a Buchi digital melting-point

apparatus and were uncorrected. Infrared (IR) spectra were recorded in KBr pellets on a

Perkin–Elmer 100 Fourier transform (FT)-IR spectrophotometer. H NMR and ¹³C

NMR spectra were measured on a Varian 400 spectrometer using CDCl₃and DMSO-

d₆as solvent and tetramethylsilane (TMS) as internal standard. Chemical shifts are given

in parts per million, and coupling constants J are in hertz. Elemental analyses were per-

formed on a Carlo Erba 1106 CHN analyzer. A monomode CEM-Discover microwave

was used in the standard conﬁguration as delivered, including proprietary software.

All experiments were carried out in microwave process vials (30 mL) with control of

the temperature by IR detection temperature sensor. The temperature was computer

monitored and maintained by discrete modulation of delivered microwave power. After

completion of the reaction, the vial was cooled to 60^ꢀC by air jet cooling.

General Procedure for the Synthesis of Compounds 2a–j Under

Conventional Conditions

A mixture of the corresponding (N⁰-ethoxycarbonyl)-4-alkyl(aryl)hydrazonic

acid ethyl ester (1a–j) (0.01 mol) and p-aminobenzophenone (0.01 mol) was heated

in an oil bath for 5 h (monitored by TLC, ethylacetate–hexane, 3:1) at 170 ^ꢀC. The

crystals formed on cooling were recrystallized from ethyl acetate–petroleum ether

(3:1) to give pure 2a–j.

General Procedure for the Synthesis of Compounds 2a–j in a

Monomode Microwave Synthesizer

A mixture of the corresponding (N⁰-ethoxycarbonyl)-4-alkyl(aryl)hydrazonic

acid ethyl ester (1a–j) (0.01 mol) and p-aminobenzophenone (0.01 mol) was irra-

diated in closed vessels with pressure control at 150 ^ꢀC for 3 min (hold time) at

300 W maximum power. After the completion of the reaction (monitored by TLC,

AcOEt=hexane, 3:1) the crystals formed on cooling were recrystallized from ethyl

acetate–petroleum ether (3:1) to give pure 2a–j.

General Procedure for the Synthesis of Compounds 3a–j Under

Conventional Condition

A mixture of the 2a–j (0.01 mol), NaBH₄(0.03 mol), and amberlyst-15 (H^þ)

(5 g) was stirred at room temperature for 12 h in dry tetrahydrofurane (100 mL)

(monitored by TLC, ethylacetate–hexane, 3:1). The reaction mixture was ﬁltered.

The solvent was removed under reduced pressure. The residue was recrystallized

from ethyl acetate–petroleum ether (3:1) to give pure 3a–j.

General Procedure for the Synthesis of Compounds 3a–j in a

Monomode Microwave Synthesizer

A mixture of 2a–j (0.01 mol), NaBH₄(0.03 mol) and neutral alumina (9.5 g)

was added in a pyrex open vessel (30 mL) and microwave irradiated at 150 ^ꢀC for

SYNTHESIS AND REDUCTION OF TRIAZOLES

1335

2 min (hold time) at 300 W maximum power. Completion of the reaction was indi-

cated by TLC (ethylacetate–hexane, 3:1). The reaction mass was eluted with ethanol

and 25 mL of water was added and heated for 10 min. The solvent was removed

under reduced pressure. The residue was recrystallized from ethyl acetate–petroleum

ether (3:1) to give pure 3a–j.

MICROBIOLOGY

All test microorganisms were obtained from the Hifzissihha Institute of Reﬁk

Saydam (Ankara, Turkey) and were as follows: Escherichia coli (E. coli)

ATCC35218, Yersinia pseudotuberculosis (Y. pseudotuberculosis) ATCC911, Pseudo-

monas aeruginosa (P. aeruginosa) ATCC43288, Enterococcus faecalis (E. faecalis)

ATCC29212, Staphylococcus aureus (S. aureus) ATCC25923, Bacillus cereus (B. cer-

eus) 709 Roma, Mycobacterium smegmatis (M. smegmatis) ATCC607, Candida albi-

cans (C. albicans) ATCC60193, and Saccharomyces cerevisiae (S. cerevisia) RSKK

251. All the newly synthesized compounds were weighed and dissolved in dimethyl-

sulfoxide (DMSO) to prepare extract stock solution of 10.000 mg=ml.

The antimicrobial effects of the substances were tested quantitatively in respect-

ive broth media by using double microdilution, and the minimal inhibition concen-

tration (MIC) values (mg=ml) were determined.^[27]The antibacterial and antifungal

assays were performed in Mueller-Hinton broth (MH) (Difco, Detroit, MI) at pH

7.3 and buffered yeast nitrogen base (Difco, Detroit, MI) at pH 7.0, respectively.

The microdilution test plates were incubated for 18–24 h at 35 ^ꢀC. Brain heart

infusion broth (BHI) (Difco, Detriot, MI) was used for M. smegmatis and incubated

for 48–72 h at 35 ^ꢀC.^[28]The MIC was deﬁned as the lowest concentration that showed

no growth. Ampicillin (10.000 mg g=ml), streptomycin 10.000 mg g=ml, and ﬂucona-

zole (2.000 mg g=ml) were used as standard antibacterial and antifungal drugs,

respectively. Dimethylsulfoxide with dilution of 1:10 was used as solvent control.

SUPPLEMENTARY INFORMATION

Full experimental details for all experiments are given in the Supplementary

Information, available online.

ACKNOWLEDGMENT

Financial support from the Scientiﬁc and Technical Research Council of

Turkey (TUBITAK) through Project 108T221 is gratefully acknowledged.

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Ecofriendly solventless synthesis and reduction reaction of some triazole compounds and evaluation of their antimicrobial activity

DOI: 10.1080/00397911.2011.632831

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Article abstract of DOI:10.1080/00397911.2011.632831

Full text of DOI:10.1080/00397911.2011.632831

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