New Azomethine Derivatives of 3-substituted-4H-4-amino-5-

ethoxycarbonyl-methylsulfanyl-1,2,4-triazoles as Potential
Anti-inflammatory Agents

IONUT VALENTIN LEDETI1,2, VASILE NICOLAE BERCEAN1*, IONUT MIHAI TANASE1, ANDREEA ANDA CREANGA1,3,
VALENTIN BADEA1, CAROL CSUNDERLIK1
1
Politehnica University Timioara, Faculty of Industrial Chemistry and Environmental Engineering, 6 Carol Telbisz, 300001
Timioara, Romania.
2
VICTOR BABE University of Medicine and Pharmacy, Faculty of Pharmacy, 2 E. Murgu Square, 300041, Timioara, Romania
3
Victor Babes University of Medicine and Pharmacy, Faculty of Medicine, 2 E. Murgu Square, 300041, Timioara, Romania

A microwave-assisted syntheses of some Schiff-base via condensation of 3-substituted-4H-4-amino-5-

ethoxycarbonyl-methylsulfanyl-1,2,4-triazoles with aromatic aldehydes without solvent is described.
Keywords: Schiff base, 1,2,4-triazole, microwave assisted synthesis

Schiff base (azomethine) derived from 4H-4-amino- A. The alkylation of 3-substituted-4H-4-amino-5-

1,2,4-triazoles attracted growing interest due to mercapto-1,2,4-triazoles (1) to 3-substituted-4H-4-amino-
analgesic[1], anticancer[1], anti-inflammator y[1], 5-ethoxycarbonyl-methylsulfanyl-1,2,4-triazole (2)
anticonvulsant[1,2], antifungal[2] and antimicrobial [1,3,4] followed by their conversion into Schiff bases (3).
properties. Also, Schiff bases containing triazoles are B. Obtaining Schiff bases (4) from 3-substituted-4H-4-
interesting bridging ligands in the coordination chemistry amino-5-mercapto-1,2,4-triazoles (1), followed by ethyl
of metal ions [5-8]. On the other hand, non-steroidal anti- chloroacetate alkylation, leading to new alkylated Schiff
inflamatory drugs containing acetate moiety are used in bases (3).
the treatment of pain and inflamation [9]. First time, we chose route A.
There is also a posibility, recently mentioned in literature, Synthesis of azomethine compound is usually carried
to attach triazoles and their derivatives to mono- out in organic medium, acid or base catalyzed, by refluxing
saccharides, in order to obtain new physiologically active the carbonyl and the amino compounds in the desired
compounds[10-12]. molar ratio[13], and for the synthesis of Schiff bases derived
For this reason, our concerns are directed towards from 3-substituted-4H-4-amino-5-mercapto-1,2,4-triazoles
obtaining new Schiff bases derived from 3-substituted-4H- (1), literature data indicate their reaction with carbonyl
4-amino-5-ethoxycarbonyl-methylsulfanyl-1,2,4-triazoles compounds in various conditions: ethanol in the presence
(2), compounds with potential biological activity and an of acetic acid [14], in presence of an excess amount of
increased capacity of complexing metal cations. concd. sulphuric acid [15], in presence of diluted HCl (at
For the synthesis of Schiff bases derived from 3- pH=5-6) [16], or in presence of piperidine [17].
substituted-4H-4-amino-5-ethoxycarbonyl-methylsulfanyl- After several attempts using above-mentioned reaction
1,2,4-triazoles, are essentially two possible routes (scheme conditions, the complete conversion of raw materials into
1): Schiff bases failed, we resorted to using microwave-
assisted synthesis method, more often indicated in
literature [18,19].

Scheme 1. The synthesis of the azomethines (3a-b) derived from

3-substituted-4H-4-amino-5-ethoxycarbonyl-methylsulfanyl-1,2,4-triazoles

* email: [email protected]

REV. CHIM. (Bucharest) 61 Nr. 10 2010 http://www.revistadechimie.ro 937

 C-NMR C (DMSO- d6, 100MHz): 168.0 (C=O); 163.8
13

Experimental Part (-CH=N-); 151.6 (3-C); 145.8 (5-C); 135.5 (1-C); 132.3
Matherials and methods (2-C, 6-C); 130.8 (1-C); 130.5 (3-C, 5-C); 128.6 (2-C,
The reagents were commercial products and used 6-C); 128.4 (3-C, 5-C); 126.72 (4-C); 126.70 (4-C); 61.1
without further purification. 4H-4-amino-5-mercapto-3- (-O-CH2-); 34.4 (-S-CH2-); 30.7 (Ph-CH2-); 13.8 (-CH3)
phenyl-1,2,4-triazole (1a, R=C6H5-) and 4-H-4-amino-3-
phenyl-5-ethoxycarbonyl-methylsulfanyl-1,2,4-triazole (2a, Results and discussion
R=C6H5-) were prepared according to the literature [20,21] In our preliminary attempts to obtain the azomethinic
and 4H-4-amino-3-benzyl-5-mercapto-1,2,4-triazole (1b, compounds 3a-d, 6a-d derived from 3-substituted-4H-4-5-
R=C6H5-CH2-) and 4H-4-amino-3-benzyl-5-ethoxycarbonyl- ethoxycarbonyl-methylsulfanyl-1,2,4-triazoles (2a-b) or 3-
methylsulfanyl-1,2,4-triazole (2b, R=C6H5-CH 2-) were substituted-4H-4-amino-5-carboxymethylsulfanyl-1,2,4-
obtained by our own method [22]. triazoles (5a-b) and substituted benzaldehydes (4-
The microwave-assisted synthesis of azomethines was bromobenzaldehyde, 4-nitro-benzaldehyde, 2-hydroxy-
carried out in a 1100 W Emerson domestic owen. Melting benzaldehyde) following the literature data, as a reaction
points were determined on a Betius PHMK (Veb Analytik medium we use absolute ethanol in the absence or
Dresden) instrument, and thin-layer chromatography was presence of acid catalysts (5% acetic acid, <1% concd.
carried out on silica gel-coated plates 60 F254 Merck using HCl, <1% concd. H2SO4 or 10% concd. H2SO4) or base
benzene:methanol 7:3 as eluant. IR spectra were recorded (piperidine) for 3-18 h reflux, respectively azeotropic
in KBr pellet on a Jasco FT/IR-410 spectrophotometer. 1H- distillation method of water formed in the reaction medium
NMR and 13C-NMR spectra were recorded on a Bruker in the presence of p-toluene sulphonic acid. In our attempts,
Avance III 400 spectrometer in DMSO-d6, using TMS as performed in the absence of catalysts, starting materials
reference; chemical shifts being reported in ppm and the did not react, and in the case of catalyzed reactions,
coupling constants in Hz. UV-VIS spectra were recorded complex mixtures containing starting materials and one
on a Jasco UV-VIS V-530 spectrophotometer. up to three products were obtained.
With our knowledge, azomethines 3a-d derived from
Microwave-assisted synthesis of azomethine from 3- 4H-4-amino-3-substituted-5-ethoxycarbonyl-
substituted-4-H-4-amino-5-ethoxycarbonyl-methylsulfanyl- methylsulfanyl-1,2,4-triazoles are not mentioned in the
1,2,4-triazoles literature. For this reason their structures were careffuly
0,9 mmol of ethoxycarbonyl-methylsulfanyl triazoles confirmed by IR, UV-VIS and NMR spectroscopy (1H-NMR,
13
(2a-b) are mixed with 0,9 mmol of corresponding C-NMR, COSY-2D, DEPT-135, HMQC and HMBC).
benzaldehyde in a 5 mL glass flask which was placed inside Analyzing the IR spectra, charactersitic vibrations of
a Teflon sealed container. The mixture was subjected to functional groups are present: esteric C=O (1737 - 1742
microwave on 800W for an optimized time. The crude cm-1), methylen (asCH2=2982-2986 cm-1, sCH2=2923-2934
products were dissolved in the minimum amount of cm-1).
absolute EtOH and allowed to crystallize over night at room As a result of electronic transitions, in UV-VIS spectra,
temperature. Products (3a-d) were separated by filtration the compounds exhibit light absorption near 393nm and at
and recrystallised from absolute ethanol. 277 (respectively 286) nm.
4H-4-(4-Nitro-benzylidene-amino)-5-benzyl-3- By analysing the NMR and IR spectroscopic results, the
ethoxycarbonyl-methylsulfanyl-1,2,4-triazole (3b) condensation reaction between 4H-4-amino-3-benzyle-5-
Yellowish powder (40% yield), m.p.=144-147 oC, ethoxycarbonyl-methylsulfanyl-1,2,4-triazole (2b, R=C6H5-
IR(KBr): 3456, 2984, 2923, 2360, 1738, 1525, 1525, 1442, CH2-) with 2-hydroxybenzaldehyde lead to a mixture
1347, 1175, 1027, 851, 731, 688, 491cm-1 (product 3d could not be separated), and the condensation
UV-VIS(methanol) [nm](x10-4) : 286.3; (1.54832) between 4H-4-amino-5-ethoxycarbonyl-methylsulfanyl-3-
1
H-NMRH (DMSO-d6, 400MHz): 9.00 (s, 1H, -CH=N-); phenyl-1,2,4-triazole(2a,R=C 6 H 5 -) and 4-bromo-
8.39 (d, 2H, J=8.6Hz, 3-H, 5-H); 8.12 (d, 2H, J=8.6Hz, benzaldehyde did not occured (product 3a was not
2-H, 6-H); 7.29-7.18 (m, 5H, 2-H, 3-H, 4-H, 5-H, 6-H); obtained).
4.34 (s, 2H, Ph-CH2-); 4.09-4.05 (m, 4H, -O-CH2-, -S-CH2-); At the same time, analyzing 2D NMR 1H-13C HMBC
1.14 (t, 3H, J=7.1Hz, -CH3) spectra of (3b), long-distance coupling 3J of phenylic
13
C-NMR C (DMSO- d6, 100MHz): 168.0 (C=O); 161.5 carbons 2-C and 6-C with azomethinic proton (-N=CH-),
3
(-CH=N-); 151.8 (3-C); 149.6 (4-C); 146.3 (5-C); 137.4 J2,6-C, -N=CH- is observed.It should be also noted that a long-
(1-C); 135.4 (1-C); 129.8 (2-C, 6-C); 128.6 (2-C, 6-C); distance coupling 2J of the carbon atom 1-C with
128.5 (3-C, 5-C); 126.8 (4-C); 124.2 (3-C, 5-C); 61.2 (- azomethinic proton N=CH-, 2J1-C, -N=CH- occurs. These long-
O-CH2-); 34.5 (-S-CH2-); 30.8 (Ph-CH2-); 13.8 (-CH3) distance couplings confirm the structure of the synthesized
compound and allow a correct assign of chemical shifts
4H-4-(4-Bromo-benzylidene-amino)-5-benzyl-3- from 1H-NMR and 13C-NMR spectra.
ethoxycarbonyl-methylsulfanyl-1,2,4-triazole (3c) The difficulty of obtaining azomethine derivatives of 3-
White powder (48% yield), m.p.=104-106 oC, substituted-4H-4-amino-5-ethoxycarbonyl-methylsulfanyl-
IR(KBr): 2982, 2934, 1742, 1614, 1592, 1442, 1305, 1173, 1,2,4-triazoles (2a, b) comparing with the facile route of
1009, 818, 727, 574, 499 cm-1 obtaining them from 3-substituted-4H-4-amino-5-
UV-VIS(methanol)[nm](x10-4): 392.6; (0.01567); mercapto-1,2,4-triazoles (1a, b) [23] finds a possible
276,7; (2.22067) explanation in tautomeric forms involved in the
1
H-NMRH (DMSO-d6, 400MHz): 8.82 (s, 1H, -CH=N-); condensation reaction with benzaldehyde. It is known that
7.80 (d, 2H, J=9.0 Hz, 3-H, 5-H); 7.78 (d, 2H, J= 9.0Hz, the condensation reaction of carbonyl compounds with
2-H, 6-H); 7.28-7.24 (m, 2H, 3-H, 5-H); 7.21-7.17 (m, amines is accomplished by the nucleophilic attack of
3H, 2-H, 4-H, 6-H); 4.65 (q, 2H, J= 7.1Hz, -O-CH2-CH3); amines to the carbonyl group, followed by the elimination
4.28 (s, 2H, Ph-CH2-); 4.05 (s, 2H, -S-CH2-); 1.14 (t, 3H, of a water molecule; the reaction occurs more readily with
J=7.1Hz, -O-CH2-CH3) the increase of the amine nucleophilicity (scheme 2).

938 http://www.revistadechimie.ro REV. CHIM. (Bucharest) 61 Nr. 10 2010

 Scheme 2. Tautomeric forms for (1a,b)
triazoles and the condensation reactions with
benzaldehydes for (1a,b) and (2a, b)

4. SUJITH, K.V., RAO, J., N., SHETTY, P., KALLURAYA, B., Eur. J. Med.
Chem. 44, nr. 9, 2009, p. 3697
The decreased reactivity of the S-alkylated compounds 5. SEN, A.,K. et al, Proc. Indian Acad. Sci. (Chem. Sci.) 110, nr.2, 1998,
2a, b can be explained by the fact that the electrone lone p. 75
pair of nitrogen from position 4 is involved in the triazolic 6. SANCAK, K., ER, M., UNVER, Y., YILDIRIM, M., DEGIRMENCIOGLU,
aromatic system, which makes the exocyclic amino group I., Transition Metal Chemistry 32, 2007, p.16
from triazoles to be an aromatic amine, slightly basic and 7. GHASSEMZADEH, M., FALL AHNEDJAD, L., HERAVI, M.M.,
a weak nucleophile. NEUMULLER, B., Polyhedron 27, 2008, p.1655
Regarding the 1a, b triazoles which prefer thionic 8. YADAV, V. K., KAR, S., L. MISHRA , Polyhedron 28, 2009, p. 121
tautomeric form [24], the aromatic conjugation cannot be 9. AL-DEEB, O. A., AL-OMAR, M.A.A., EL-BROLLOSY, N.R., HABIB,
maintained with the lone pair of the nitrogen atom from E.E., IBRAHIM, T.M., EL-AMAM, A.A., Arzneim-Forsch. Drug Res. 56,
position 4, and as a result, the exocyclic amino group is a nr. 1, 2006, p. 40
hydrazinic one, with an increased density of electrons, 10. LASCU, A., SISU, I., BERCEAN, V., LUPEA, A.X., CPROIU, M.T.,
an increased nucleophilicity, and hence an increased SISU, E., Rev. Roum. Chim. 55, no. 3, 2010, p. 205
reactivity. 11. SISU, I., BERCEAN, V., BADEA, V., CPROIU, M.T., SISU, E., Rev.Chim.
Also, the presence of benzenic nucleus in 2a compound (Bucharest), 60, no. 9, 2009, p. 884
(R = C6H5-) with the inductive effect -I, entails an additional 12. SISU, I., BERCEAN, V., NICULESCU, M., DINC, N., SISU, E.,
decrease in electron density at exocyclic amino group, Rev.Chim. (Bucharest), 56, no. 12, 2005, p. 1249
which may explain its lack of reactivity in reactions with 13. COZZI, P.,G., Chem. Soc. Rev., 33, 2004, p. 410
benzaldehydes, in contrast to compound 2b (R = C6H5- 14. BEKIRCAN, O., BEKTAS, H., Molecules 13, 2008, p. 2126
CH 2-), where inductive effect of the phenyl group is 15. YU, H.X, MA, J.F., XU, G.H., SHUN-LI, Journal of Organometallic
diminished. Chemistry 691, 2006, p. 3531
16. YE, X.X., CHEN, Z.F., ZHANG, A.J., ZHANG, L.X., Molecules 12,
Conclusion 2007, p. 1202
The condensation of 4H-4-amino-3-substituted-5- 17. BADWAIK, V. B., ASWAR, A. S., Russian Journal of Coordination
ethoxycarbonyl-methylsulfanyl-1,2,4-triazoles (2a,b) with Chemistry 33, nr. 10, 2007, p. 755
substituted benzaldehydes under microwave irradiation 18. Microwaves in Organic Synthesis, 2nd edition, 2, Wiley-VCH Verlag
lead with medium yields to corresponding Schiff bases, GmbH & Co. KGaA, Loupy A. (editor), Weinheim, 2006, p.807
unlike the methods of condensation in organic solvent in 19. YANG, H., J., SUN, W., H., LI, Z., L., MA, Z., Chin. Chem. Lett. 13,
the presence of acid or alkaline catalysts, which lead to nr. 1, 2002, p. 3
mixtures. 20. HOGGARTH, E., J.Chem.Soc., 1952, p. 4811
21. LEDEI, I.V., BERCEAN, V.N., BADEA, V., BLAN, M., CSUNDERLIK,
References C., Rev. Chim. (Bucharest), 61, no. 9, 2010, p. 833
1. ISLOOR, A.M., KALLURAYA, B., SHETTY, P., Eur. J. Med. Chem. 44, 22. LEDEI, I.V., BERCEAN, V.N., BADEA, V., BLAN, M., CSUNDERLIK,
nr. 9, 2009, p. 3784 C., (unpublished results)
2. KHANMOHAMMADI, H., ABNOSI, M., H., HOSSEINZADEH, A., 23. CREANG A.A., BERCEAN V.N., LEDEI I.V., BADEA V. (unpublished
ERFANTALAB, M., Spectrochimica Acta: Part A 71, 2008, p. 1474 results)
3. BAYRAK, H., DEMIRBAS, A., KARAOGLU, S., A., DEMIRBAS, N., Eur. 24. Advances in Heterocyclic Chemistry 76, Academic Press, Katritzky,
J. Med. Chem. 44, nr. 9, 2009, p. 1057 A.R. (Ed.), Elguero, J., Denisova, O. V., 2000, p. 234

Manuscript received: 15.06.2010

REV. CHIM. (Bucharest) 61 Nr. 10 2010 http://www.revistadechimie.ro 939

 Asociaia Grupul pentru Reform i Alternativ Universitar (GRAUR)
Cluj-Napoca
Indexul Operelor Plagiate n Romnia
www.plagiate.ro

Decizie de indexare a faptei de plagiat la poziia

00059 / 07.07.2013
i pentru admitere la publicare n volum tiprit
care se bazeaz pe:

A. Nota de constatare i confirmare a indiciilor de plagiat prin fia suspiciunii inclus

n decizie.

Fia suspiciunii de plagiat / Sheet of plagiarisms suspicion

Opera suspicionat (OS) Opera autentic (OA)

Suspicious work Authentic work
OS BOJI, M.; ROMAN, L.; SNDULESCU, R. i OPREAN, R. Analiza i controlul medica-
mentelor, vol.2: Metode instrumentale n analiza i controlul medicamentelor. Deva:
Intelcredo. 2003.
OA BEEBE, K.R.; PELL, R.J. and SEASHOLTZ, M.B. Chemometrics: A Practical Guide. John
Willy & Sons, 1998.
Incidena minim a suspiciunii / Minimum incidence of suspicion
p.677:20 p.694:21 p.27:01 p.44:27
p.678: Figura 16.1 p.28: Figure 3.1
p.679: Figura 16.2 p.29: Figure 3.2
p.681: Figura 16.3 p.31: Figure 3.3
p.682: Figura 16.4 p.32: Figure 3.4
p.683: Figura 16.5 p.33: Figure 3.5
p.683: Figura 16.6 p.34: Figure 3.6
p.684: Figura 16.7 p.34: Figure 3.7
p.685: Figura 16.8 p.35: Figure 3.8
p.686: Tabelul 16.1 p.36: Table 3.2
p.687: Figura 16.9 p.37: Figure 3.9
p.687: Figura 16.10 p.38: Figure 3.10
p.688: Figura 16.11 p.39: Figure 3.11
p.688: Tabelul 16.2 p.40: Table 3.3
p.690: Figura 16.12 p.40: Figure 3.12
p.690: Figura 16.13 p.41: Figure 3.13
p.692: Figura 16.14 p.42: Figure 3.14
p.693: Figura 16.15 p.43: Figure 3.15
p.694: Figura 16.16 p.45: Figure 3.16
Fia ntocmit pentru includerea suspiciunii n Indexul Operelor Plagiate n Romnia de la
Sheet drawn up for including the suspicion in the Index of Plagiarized Works in Romania at
www.plagiate.ro
Not: Prin p.72:00 se nelege paragraful care se termin la finele pag.72. Notaia p.00:00 semnific pn la ultima
pagin a capitolului curent, n ntregime de la punctul iniial al prelurii.
Note: By p.72:00 one understands the text ending with the end of the page 72. By p.00:00 one understands the
taking over from the initial point till the last page of the current chapter, entirely.
B. Fia de argumentare a calificrii de plagiat alturat, fi care la rndul su este
parte a deciziei.

Echipa Indexului Operelor Plagiate n Romnia

 Asociaia Grupul pentru Reform i Alternativ Universitar (GRAUR)
Cluj-Napoca
Indexul Operelor Plagiate n Romnia
www.plagiate.ro

Fia de argumentare a calificrii

Nr. Descrierea situaiei care este ncadrat drept plagiat Se
crt. confirm
1. Preluarea identic a unor pasaje (piese de creaie de tip text) dintr-o oper autentic publicat, fr precizarea ntinderii i menionarea

provenienei i nsuirea acestora ntr-o lucrare ulterioar celei autentice.
2. Preluarea a unor pasaje (piese de creaie de tip text) dintr-o oper autentic publicat, care sunt rezumate ale unor opere anterioare operei
autentice, fr precizarea ntinderii i menionarea provenienei i nsuirea acestora ntr-o lucrare ulterioar celei autentice.
3. Preluarea identic a unor figuri (piese de creaie de tip grafic) dintr-o oper autentic publicat, fr menionarea provenienei i nsuirea

acestora ntr-o lucrare ulterioar celei autentice.
4. Preluarea identic a unor tabele (piese de creaie de tip structur de informaie) dintr-o oper autentic publicat, fr menionarea

provenienei i nsuirea acestora ntr-o lucrare ulterioar celei autentice.
5. Republicarea unei opere anterioare publicate, prin includerea unui nou autor sau de noi autori fr contribuie explicit n lista de autori
6. Republicarea unei opere anterioare publicate, prin excluderea unui autor sau a unor autori din lista iniial de autori.
7. Preluarea identic de pasaje (piese de creaie) dintr-o oper autentic publicat, fr precizarea ntinderii i menionarea provenienei, fr
nici o intervenie personal care s justifice exemplificarea sau critica prin aportul creator al autorului care preia i nsuirea acestora ntr-o
lucrare ulterioar celei autentice.
8. Preluarea identic de figuri sau reprezentri grafice (piese de creaie de tip grafic) dintr-o oper autentic publicat, fr menionarea
provenienei, fr nici o intervenie care s justifice exemplificarea sau critica prin aportul creator al autorului care preia i nsuirea acestora
ntr-o lucrare ulterioar celei autentice.
9. Preluarea identic de tabele (piese de creaie de tip structur de informaie) dintr-o oper autentic publicat, fr menionarea provenienei,
fr nici o intervenie care s justifice exemplificarea sau critica prin aportul creator al autorului care preia i nsuirea acestora ntr-o lucrare
ulterioar celei autentice.
10. Preluarea identic a unor fragmente de demonstraie sau de deducere a unor relaii matematice care nu se justific n regsirea unei relaii
matematice finale necesare aplicrii efective dintr-o oper autentic publicat, fr menionarea provenienei, fr nici o intervenie care s
justifice exemplificarea sau critica prin aportul creator al autorului care preia i nsuirea acestora ntr-o lucrare ulterioar celei autentice.
11. Preluarea identic a textului (piese de creaie de tip text) unei lucrri publicate anterior sau simultan, cu acelai titlu sau cu titlu similar, de un
acelai autor / un acelai grup de autori n publicaii sau edituri diferite.
12. Preluarea identic de pasaje (piese de creaie de tip text) ale unui cuvnt nainte sau ale unei prefee care se refer la dou opere, diferite,
publicate n dou momente diferite de timp.

Not:

a) Prin provenien se nelege informaia din care se pot identifica cel puin numele autorului / autorilor, titlul operei, anul apariiei.

b) Plagiatul este definit prin textul legii1.

plagiatul expunerea ntr-o oper scris sau o comunicare oral, inclusiv n format electronic, a unor texte, idei, demonstraii, date, ipoteze,
teorii, rezultate ori metode tiinifice extrase din opere scrise, inclusiv n format electronic, ale altor autori, fr a meniona acest lucru i fr a
face trimitere la operele originale.
Tehnic, plagiatul are la baz conceptul de pies de creaie care2:
este un element de comunicare prezentat n form scris, ca text, imagine sau combinat, care posed un subiect, o organizare sau o
construcie logic i de argumentare care presupune nite premise, un raionament i o concluzie. Piesa de creaie presupune n mod necesar
o form de exprimare specific unei persoane. Piesa de creaie se poate asocia cu ntreaga oper autentic sau cu o parte a acesteia
cu care se poate face identificarea operei plagiate sau suspicionate de plagiat3:
O oper de creaie se gsete n poziia de oper plagiat sau oper suspicionat de plagiat n raport cu o alt oper considerat autentic
dac:
i) Cele dou opere trateaz acelai subiect sau subiecte nrudite.
ii) Opera autentic a fost fcut public anterior operei suspicionate.
iii) Cele dou opere conin piese de creaie identificabile comune care posed, fiecare n parte, un subiect i o form de prezentare bine
definit.
iv) Pentru piesele de creaie comune, adic prezente n opera autentic i n opera suspicionat, nu exist o menionare explicit a
provenienei. Menionarea provenienei se face printr-o citare care permite identificarea piesei de creaie preluate din opera autentic.
v) Simpla menionare a titlului unei opere autentice ntr-un capitol de bibliografie sau similar acestuia fr delimitarea ntinderii prelurii
nu este de natur s evite punerea n discuie a suspiciunii de plagiat.
vi) Piesele de creaie preluate din opera autentic se utilizeaz la construcii realizate prin juxtapunere fr ca acestea s fie tratate de
autorul operei suspicionate prin poziia sa explicit.
vii) In opera suspicionat se identific un fir sau mai multe fire logice de argumentare i tratare care leag aceleai premise cu aceleai
concluzii ca n opera autentic

1 Legea nr. 206/2004 privind buna conduit n cercetarea tiinific, dezvoltarea tehnologic i inovare, publicat n Monitorul Oficial al Romniei, Partea I, nr. 505

din 4 iunie 2004

2 ISOC, D. Ghid de aciune mpotriva plagiatului: bun-conduit, prevenire, combatere. Cluj-Napoca: Ecou Transilvan, 2012.
3 ISOC, D. Prevenitor de plagiat. Cluj-Napoca: Ecou Transilvan, 2014.