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Synthesis of some novel bis-1,2,4-triazole and bis-1,3,4-thiadiazole derivatives from terephthaloyl and isophthaloyl chlorides

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Published/Copyright: July 5, 2013
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Heterocyclic Communications
From the journal Heterocyclic Communications Volume 19 Issue 4

Abstract

An efficient synthesis of novel bis-1,2,4-triazole and bis-1,3,4-thiadiazole derivatives starting from terephthaloyl and isophthaloyl chlorides is described. Terephthaloyl or isophthaloyl chloride was allowed to react with hydrazine hydrate in refluxing ethanol to give a corresponding bis-hydrazide derivative. Further reaction of these compounds with isothiocyanates gave bis-thiosemicarbazide derivatives, which then underwent cyclization to bis-1,3,4-thiadiazoles in the presence of sulfuric acid. The cyclization of these compounds in the presence of sodium hydroxide resulted in the formation of bis-1,2,4-triazole-3-thioles. The structure of these compounds was characterized by IR, NMR, and elemental analysis.

Keywords: thiadiazole; thiosemicarbazide; triazole

Introduction

Recently, special attention has been focused on the synthesis of heterocyclic compounds which exhibit a wide range of biological activities, including antibacterial, antifungal, and other properties [1–6]. A literature survey has revealed that 1,2,4 triazole derivatives are interesting drug candidates including central nervous system stimulants, sedatives, and anti-inflammatory, antianxiety, antimicrobial [7, 8], antitubercular [9], antihypertensive [10], and antiasthmatic agents [11].

Several potent drug compounds possessing the triazole ring have been used in medicine. These are alprazolam (anxiolytic agent, tranquilizer), estazolam (hypnotic, sedative, tranquilizer), nefazodone (antidepressant, 5-HT2 A-antagonist), and triazolam (sedative and hypnotic) [12]. The 1,2,4-triazole moiety exists in the structure of various natural products [13]. 1,3,4-Thiadiazoles are drug candidates as anti-parkinsonism [14], hypoglycemic [15], and antihypertensive [16] agents. The activity of 1,3,4-thiadiazoles is probably due to the presence of the =N-C-S moiety [17]. Thiosemicarbazides are also associated with many pharmacological activities. The synthesis of bis-heterocyclic compounds, which show various biological activities [18–21], have been the subject of extensive study in recent years.

In view of these facts and in continuation of our work on the synthesis of heterocyclic compounds containing nitrogen and sulfur [22–24] and bis-heterocyclic compounds [25–28] with expected biological activity, the aim of the present study was to prepare new bis-1,2,4-triazole and bis-1,3,4-thiadiazole derivatives.

Results and discussion

Phthaloyl and isophthaloyl chlorides 1a,b are excellent building blocks for the synthesis of new series of bis-heterocyclic compounds 4a–f and 5a–f as depicted in Scheme 1. Compounds 1a,b were converted to bis-(acid hydrazides) 2a,b by the reaction with hydrazine hydrate in ethanol.

Scheme 1
Scheme 1

The IR spectrum of compound 2a shows absorption bands at 3300, 3230, 3030, and 1714 cm-1 corresponding to the NH, NH2, CH-aromatic, and C=O stretching vibration groups, respectively. The 1H NMR spectrum of this compound contains a broad singlet at δ 4.50 for two NH2 groups, exchangeable with D2O, and a doublet for NH group at δ 9.90. The 13C NMR spectrum of 2a shows signals at δ 127.4, 135.9, and 165.6 due to resonance of aromatic carbons and a carbonyl group. The IR, 1H NMR, and 13C NMR spectra of other bis-(acid hydrazides) show similar features.

Treatment of compounds 2a,b with various substituted isothiocyanates gave bis-thiosemicarbazide derivatives 3a,f. The IR spectrum of 3b displays absorption bands at 3319, 3240, 2970, 2931, 1680, and 1246 cm-1 corresponding to NH, CH-Ar, CH-aliphatic, C=O, and C=S groups, respectively. The 1H NMR spectrum of this compound reveals a triplet at δ 1.07 due to the resonance of two CH3 protons, a quartet for two CH2 groups, and a singlet for Ar-H protons at δ 8.00. The 13C NMR spectrum of compound 3b shows peaks at δ 14.9, 39.00, 128.2, 135.8, 165.8, and 181.9 corresponding to aliphatic C-H, aromatic C-H, C=S, and C=O groups. The IR, 1H NMR, and 13C NMR spectra of other bis-thiosemicarbazide derivatives show similar absorption bands.

Bis-thiosemicarbazides 3a–f on heating with 2 N NaOH in ethanol underwent smooth cyclization through dehydration to afford bis(1,2,4-triazoles-3-thiols) 4a–f. The IR spectrum of 3e displays absorption bonds at 1676 cm-1 due to C=N and at 2766 cm-1 corresponding to an SH group. The formation of bis-triazole moiety is further supported by its 1H NMR spectrum, which shows a triplet for resonance of CH3 protons at δ 1.15, a multiplet at δ 7.76–7.99 ppm for four aromatic protons and a singlet for an SH proton at δ 14.00, exchangeable with D2O. The 13C NMR spectrum of compound 4e shows six different peaks for aromatic and aliphatic carbons in the expected regions and the signals at δ 150.7 and 167.4 assigned to C=S and C=O groups. The IR, 1H NMR, and 13C NMR spectra of other products 4 show similar absorption bands.

5,5′-Phenylene-bis(2-substituted phenyl/alkyl diamino-1,3,4-thiadiazoles) 5a–f were obtained by cyclization of 3a–f by treatment with cold concentrated sulfuric acid. The IR spectrum of compound 5d shows absorption bands at 1539 cm-1 due to C=N stretching vibrations. The 1H NMR and 13C NMR spectra of 5a–f are fully consistent with their structures.

Conclusion

A simple and efficient method for preparation of bis-1,2,4-triazole and bis-1,3,4-thiadiazole derivatives was developed. This procedure offers several advantages such as good yields of cyclization products, short reaction times, and simple purification.

Experimental

General

All chemicals were obtained from Merck or Aldrich Companies. Melting points were determined in open capillary tubes on an electrothermal digital apparatus and are uncorrected. Reactions were monitored by thin layer chromatography (TLC) on Merck silica gel (60 GF254) plates (0.25 mm). All yields refer to isolated products. IR spectra were recorded on a Galaxy FTIR 5000 spectrophotometer using KBr discs. 1H NMR spectra (300 MHz) and 13C NMR spectra (75 MHz) were recorded on a Brucker spectrophotometer in DMSO-d6 using tetramethylsilane (TMS) as an internal standard. Microanalyses were performed on a Vario EL III instrument at Arak University.

General procedure for the synthesis of hydrazides 2a,b

Terephthaloyl chloride 1a or isophthaloyl chloride 1b (1 mmol) and hydrazine hydrate (4 mmol) were dissolved in ethanol (50 mL) and the solution was heated under reflux for 8–10 h. After completion of the reaction, the obtained solid was filtered and crystallized from ethanol.

Terephthalohydrazide (2a)

Yield 92%; mp > 300°C; IR: 3300 and 3230 (NH, NH2), 3030 (CH-aromatic), 1714 cm-1 (C=O); 1H NMR: δ 4.50 (bs, 4H, 2NH2, exchangeable with D2O), 7.87 (s, 4H, Ar-H), 9.90 (s, 2H, 2NH, exchangeable with D2O); 13C NMR: 127.4 (CH), 135.9 (CH), 165.6 (CO). Anal. Calcd for C8H10N4O2: C, 49.48; H, 5.19; N, 28.85. Found: C, 49.68; 5.01; N, 28.59.

Isophthalohydrazide (2b)

Yield 91%; mp 232–234°C; IR: 3296 and 3220 (NH, NH2), 1678 cm-1 (C=O); 1H NMR: δ 4.53 (bs, 4H, 2NH2, exchangeable with D2O), 7.49–7.54 (q, 1H, Ar-H), 7.90, 7.92 (d, 2H, Ar-H), 8.25 (s, 1H, Ar-H), 9.82 (s, 2H, 2NH, exchangeable with D2O); 13C NMR: δ 126.5 (CH), 128.9 (CH), 129.7 (CH), 134.0 (CH), 165.9 (CO). Anal. Calcd for C8H10N4O2: C, 49.48; H, 5.19; N, 28.85. Found: C, 49.27; H, 5.41; N, 28.98.

General procedure for the synthesis of bis-terephthaloyl and isophthaloyl thiosemicarbazides 3a–f

A mixture of 2a or 2b (1.95 g, 10 mmol) and methyl, ethyl or phenyl isothiocyanate (20 mmol) in absolute ethanol (50 mL) was heated under reflux for 7 h. The mixture was cooled and filtered. The obtained precipitate was crystallized from DMF-H2O (2:1) to afford the corresponding bis-thiosemicarbazide derivative 3a–f.

Terephthaloyl bis(N-methylhydrazino-2-thiocarbamide) (3a)

Yield 94%; mp 235–237°C; IR: 3252 and 3203 (NH), 2980 (CH-Ar), 2939 (CH3), 1676 (C=O), 1251 cm-1 (C=S); 1H NMR: 2.88 (s, 6H, 2CH3), 8.00 (s, 4H, Ar-H), 8.10 (s, 2H, NH-NH, exchangeable with D2O), 9.37 (s, 2H, NH, exchangeable with D2O), 10.47 (s, 2H, NH, exchangeable with D2O); 13C NMR: δ 31.4, 128.2, 135.7, 165.9, 182.7. Anal. Calcd for C12H16N6O2S2: C, 42.34; H, 4.74; N, 24.69; S, 18.84. Found: C, 42.21; H, 4.89; N, 24.50; S, 18.74.

Terephthaloyl bis(N-ethylhydrazino-2-thiocarbamide) (3b)

Yield 95%; mp 233–234°C; IR: 3319–3240 (NH), 2970 (CH-Ar), 2931 (CH3), 1680 (C=O), 1246 cm-1 (C=S); 1H NMR: δ 1.07 (t, 6H, 2CH3, J = 7 Hz), 3.48 (q, 4H, 2CH2, J = 7 Hz), 8.00 (s, 4H, Ar-H), 8.14 (s, 2H, NH, exchangeable with D2O), 9.26 (s, 2H, NH, exchangeable with D2O), 10.44 (s, 2H, NH, exchangeable with D2O); 13C NMR: δ 14.9, 39.0, 128.2, 135.8, 165.8, 181.9. Anal. Calcd for C14H20N6O2S2: C, 45.63; H, 5.47; N, 22.81; S, 17.40. Found: C, 45.46; H, 5.53; N, 22.74; S, 17.29.

Terephthaloyl bis(N-phenylhydrazino-2-thiocarbamide) (3c)

Yield 96%; mp 221–223°C; IR: 3259–3175 (NH), 2928 (CH-Ar), 1672 (C=O), 1253 cm-1 (C=S); 1H NMR: δ 7.14–8.05 (m, 14H, Ar-H), 9.73 (s, 2H, NH, exchangeable with D2O), 9.86 (s, 2H, NH, exchangeable with D2O), 10.68 (s, 2H, NH, exchangeable with D2O); 13C NMR: δ 125.6, 126.6, 128.3, 128.5, 135.8, 139.7, 162.8, 165.9, 181.6. Anal. Calcd for C22H20N6O2S2: C, 56.88; H, 4.34; N, 18.09; S, 13.80. Found: C, 56.71; H, 4.39; N, 17.95; S, 13.88.

Isophthaloyl bis(N-methylhydrazino-2-thiocarbamide) (3d)

Yield 90%; mp 197–199°C; IR: 3302 and 3203 (NH), 3005 (CH-Ar), 2939 (CH3), 1683 (C=O), 1253 cm-1 (C=S); 1H NMR: δ 2.88 (s, 6H, 2CH3), 7.57–8.01(m, 4H, Ar-H), 8.42 (s, 2H, NH, exchangeable with D2O), 9.35 (s, 2H, NH, exchangeable with D2O), 10.43 (s, 2H, NH, exchangeable with D2O); 13C NMR: δ 31.4, 128.2, 130.6, 131.3, 133.2, 166.0, 182.8. Anal. Calcd for C12H16N6O2S2: C, 42.34; H, 4.74; N, 24.69; S, 18.84. Found: C, 42.17; H, 4.89; N, 24.51; S, 18.79.

Isophthaloyl bis(N-ethylhydrazino-2-thiocarbamide) (3e)

Yield 92%; mp 207–209°C; IR: 3311–3180 (NH), 2974 (CH-Ar), 2931 (CH3), 1676 (C=O), 1242 cm-1 (C=S); 1H NMR: δ 1.06 (t, 6H, 2CH3, J = 7 Hz), 3.45–3.50 (q, 4H, 2CH2, J = 7 Hz), 8.08–8.43 (m, 4H, Ar-H), 8.11 (s, 2H, NH, exchangeable with D2O), 9.28 (s, 2H, NH, exchangeable with D2O), 10.41 (s, 2H, NH, exchangeable with D2O); 13C NMR: δ 14.9, 39.0, 128.2, 128.6, 131.3, 133.2, 165.9, 181.9. Anal. Calcd for C14H20N6O2S2: C, 45.63; H, 5.47; N, 22.81; S, 17.40. Found: C, 45.47; H, 5.58; N, 22.67; S, 17.32.

Isophthaloyl bis(N-phenylhydrazino-2-thiocarbamide) (3f)

Yield 89%; mp 191–192°C; IR: 3184–3113 (NH), 2939 (CH-Ar), 1676 (C=O), 1207 cm-1 (C=S); 1H NMR: δ 7.15–8.21 (m, 14H, Ar-H), 8.58 (s, 2H, NH, exchangeable with D2O), 9.94 (s, 2H, NH, exchangeable with D2O), 10.68 (s, 2H, NH, exchangeable with D2O); 13C NMR: δ 125.7, 126.5, 128.6, 129.5, 131.5, 133.2, 139.6, 166.1, 181.9. Anal. Calcd for C22H20N6O2S2: C, 56.88; H, 4.34; N, 18.09; S, 13.80. Found: C, 56.92; H, 4.47; N, 17.89; S, 13.71.

General method for the synthesis of bis(1,2,4-triazole-3-thiols) 4a–f

A suspension of 3a–f (2 mmol) in ethanol (25 mL) was dissolved in aqueous sodium hydroxide (2 N, 2 mL) and the solution was heated under reflux for 4 h. Then, the solution was concentrated, cooled, and filtered. The filtrate was adjusted to pH ~4–5 with hydrochloric acid and kept at room temperature for 1 h. The obtained product was filtered, washed with water, dried, and crystallized from DMF-H2O.

5,5′-(1,4-Phenylene)-bis(4-methyl-4H-1,2,4-triazole-3-thiol) (4a)

Yield 88%; mp > 300°C; IR: 3111 (NH), 3032 (CH-Ar), 2933 (CH3), 2756 (S-H), 1564, 1520 (C=N), 1275 cm-1 (C=S); 1H NMR: δ 3.56 (s, 6H, 2CH3), 7.93 (s, 4H, Ar-H), 14.04 (s, 2H, SH, exchangeable with D2O); 13C NMR: δ 32.2, 128.5, 129.5, 151.1, 168.2. Anal. Calcd for C12H12N6S2: C, 47.35; H, 3.97; N, 27.61; S, 21.07. Found: C, 47.21; H, 3.71; N, 27.51; S, 20.86.

5,5′-(1,4-Phenylene)bis(4-ethyl-4H-1,2,4-triazole-3-thiol) (4b)

Yield 89%; mp > 300°C; IR: 3111 (NH), 3032 (CH-Ar), 2986, 2933 (CH3), 2750 (S-H), 1566, 1518 (C=N), 1269 cm-1 (C=S); 1H NMR: δ 1.18 (t, 6H, 2CH3, J = 7 Hz), 4.08 (q, 4H, 2CH2, J = 7 Hz), 7.88 (s, 4H, Ar-H), 13.95 (s, 2H, SH, exchangeable with D2O); 13C NMR: δ 13.9, 39.2, 128.6, 128.6, 150.7, 167.7. Anal. Calcd for C14H16N6S2: C, 50.58; H, 4.85; N, 25.28; S, 19.29. Found: C, 50.41; H, 5.08; N, 25.31; S, 19.43.

5,5′-(1,4-Phenylene)bis(4-phenyl-4H-1,2,4-triazole-3-thiol) (4c)

Yield 89%; mp > 300°C; IR: 3065 (NH), 2976 (CH-Ar), 2914, 2746 (S-H), 1595, 1498 (C=N), 1273 cm-1 (C=S); 1H NMR: δ 7.03–7.46 (m, 14H, Ar-H), 14.11 (s, 2H, SH, exchangeable with D2O); 13C NMR: δ 126.7, 128.7, 129.3, 129.8, 130.4, 134.5, 151.3, 169.4. Anal. Calcd for C22H16N6S2: C, 61.66; H, 3.76; N, 19.61; S, 14.97. Found: C, 61.48; H, 3.89; N, 19.49; S, 15.15.

5,5′-(1,3-Phenylene)bis(4-methyl-4H-1,2,4-triazole-3-thiol) (4d)

Yield 86%; mp 290–292°C; IR: 3109 (NH), 3047 (CH-Ar), 2914 (CH3), 2769 (S-H), 1539, 1500 (C=N), 1275 cm-1 (C=S); 1H NMR: δ 3.56 (s, 6H, 2CH3), 7.93 (s, 4H, Ar-H), 14.04 (s, 2H, SH, exchangeable with D2O); 13C NMR: δ 32.2, 128.5, 129.5, 151.1, 168.2. Anal. Calcd for C12H12N6S2: C, 47.35; H, 3.97; N, 27.61; S, 21.07. Found: C, 47.23; H, 4.00; N, 27.59; S, 20.85.

5,5′-(1,3-Phenylene)bis(4-ethyl-4H-1,2,4-triazole-3-thiol) (4e)

Yield 90%; mp 277–279°C; IR: 3101 (NH), 3026 (CH-Ar), 2933 (CH3), 2766 (S-H), 1541, 1504 (C=N), 1280 cm-1 (C=S); 1H NMR: δ 1.15 (t, 6H, 2CH3, J = 7 Hz), 4.07 (q, 4H, 2CH2, J = 7 Hz), 7.76–7.99 (m, 4H, Ar-H), 14.00 (s, 2H, SH, exchangeable with D2O); 13C NMR: δ 13.8, 39.7, 127.4, 129.0, 130.5, 131.3, 150.7, 167.4. Anal. Calcd for C14H16N6S2: C, 50.58; H, 4.85; N, 25.28; S, 19.29. Found: C, 50.68; H, 4.90; N, 25.17; S, 19.41.

5,5′-(1,3-Phenylene)bis(4-phenyl-4H-1,2,4-triazole-3-thiol) (4f)

Yield 88%; mp > 300°C; IR: 3192 (NH), 3049 (CH-Ar), 2755 (S-H), 1601, 1550 (C=N), 1226 cm-1 (C=S); 1H NMR: δ 7.03–7.46 (m, 14H, Ar-H), 14.11 (s, 2H, SH, exchangeable with D2O); 13C NMR: δ 126.7, 128.7, 129.3, 129.8, 130.4, 134.5, 151.3, 169.4. Anal. Calcd for C22H16N6S2: C, 61.66; H, 3.76; N, 19.61; S, 14.97. Found: C, 61.79; H, 3.84; N, 19.50; S, 15.21.

General procedure for the synthesis of 5,5′-phenylene bis(N-alkyl/phenylamino-1,3,4-thiadiazoles) 5a–f

A solution of 3a–f (3 mmol) in concentrated sulfuric acid (3 mL) was stirred at room temperature for 2 h and then poured into ice-cold water. The mixture was made alkaline to pH ˜8 with aqueous ammonia and the resultant precipitate was filtered, washed with water, and crystallized from DMF-H2O.

5,5′-(1,4-Phenylene)bis(N-methyl-1,3,4-thiadiazol-2-amine) (5a)

Yield 90%; mp > 300°C; IR: 3203 (NH), 3095 (CH-Ar), 2991, 2930 (CH3), 1575, 1523 cm-1 (C=N); 1H NMR: δ 2.94 (s, 6H, 2CH3), 7.83(s, 4H, Ar-H), 7.94 (s, 2H, NH, exchangeable with D2O); 13C NMR: δ 31.8, 127.3, 132.0, 155.5, 169.9. Anal. Calcd for C12H12N6S2: C, 47.35; H, 3.97; N, 27.61; S, 21.07. Found: C, 47.62; H, 4.21; N, 27.63; S, 20.90.

5,5′-(1,4-Phenylene)bis(N-ethyl-1,3,4-thiadiazol-2-amine) (5b)

Yield 90%; mp 295–297°C; IR: 3159 (NH), 3059 (CH-Ar), 2966, 2893 (CH3), 1626, 1562 cm-1 (C=N); 1H NMR: δ 1.21 (t, 6H, 2CH3, J = 7 Hz), 3.36 (q, 4H, 2CH2, J = 7 Hz), 7.83 (s, 4H, Ar-H), 8.10 (s, 2H, NH, exchangeable with D2O); 13C NMR: δ 14.7, 40.2, 127.3, 132.1, 155.3, 169.1. Anal. Calcd for C14H16N6S2: C, 50.58; H, 4.85; N, 25.28; S, 19.29. Found: C, 50.63; H, 4.98; N, 25.33; S, 19.11.

5,5′-(1,4-Phenylene)bis(N-phenyl-1,3,4-thiadiazol-2-amine) (5c)

Yield 90%; mp > 300°C; IR: 3155 (NH), 3014 (CH-Ar), 1575, 1523 cm-1 (C=N); 1H NMR: δ 6.70 (s, 2H, NH, exchangeable with D2O) 7.16–7.95 (14H, Ar-H); 13C NMR: δ 118.2, 124.4, 128.0, 129.1, 131.7, 141.6, 156.5, 166.1. Anal. Calcd for C22H16N6S2: C, 61.66; H, 3.76; N, 19.61; S, 14.97. Found: C, 61.87; H, 3.90; N, 19.58; S, 15.69.

5,5′-(1,3-Phenylene)bis(N-methyl-1,3,4-thiadiazol-2-amine) (5d)

Yield 90%; mp 238–240°C; IR: 3171 (NH), 3092 (CH-Ar), 2939, 2864(CH3), 1566 cm-1 (C=N); 1H NMR: δ 2.94 (s, 6H, 2CH3), 7.55–8.05 (m, 4H, Ar-H), 8.11 (s, 2H, NH, exchangeable with D2O); 13C NMR: δ 31.8, 123.4, 127.8, 130.6, 132.1, 155.4, 170.0. Anal. Calcd for C12H12N6S2: C, 47.35; H, 3.97; N, 27.61; S, 21.07. Found: C, 47.18; H, 3.75; N, 27.65; S, 20.85.

5,5′-(1,3-Phenylene)bis(N-ethyl-1,3,4-thiadiazol-2-amine) (5e)

Yield 92%; mp 242–244°C; IR: 3188 (NH), 3032 (CH-Ar), 2982 (CH3), 1631, 1543 (C=N), 1178 cm-1 (C=S); 1H NMR: δ 1.20 (t, 6H, 2CH3, J = 7 Hz), 3.37 (q, 4H, 2CH2, J = 7 Hz), 6.94–7.75 (m, 4H, Ar-H), 8.15 (s, 2H, NH, exchangeable with D2O). Anal. Calcd for C14H16N6S2: C, 50.58; H, 4.85; N, 25.28; S, 19.29. Found: C, 50.81; H, 4.66; N, 25.04; S, 19.02.

5,5′-(1,3-Phenylene)bis(N-phenyl-1,3,4-thiadiazol-2-amine) (5f)

Yield 88%; mp > 300°C; IR: 3111 (NH), 3032 (CH-Ar), 2933 (CH3), 2756 (S-H), 1564, 1520 (C=N), 1275 cm-1 (C=S); 1H NMR: δ 6.99–7.87 (m, 14H, Ar-H), 8.27 (s, 2H, NH, exchangeable with D2O); 13C NMR: δ 117.1, 124.2, 127.0, 129.0, 130.9, 131.5, 141.3, 141.5, 157.6, 164.6. Anal. Calcd for C22H16N6S2: C, 61.66; H, 3.76; N, 19.61; S, 14.97. Found: C, 61.51; H, 3.83; N, 19.52; S, 15.12.

Corresponding author: Abdolhossein Rafiee, Faculty of Sciences, Department of Chemistry, Arak University, Arak 38156–879, Iran

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Received: 2013-3-3
Accepted: 2013-4-28
Published Online: 2013-07-05
Published in Print: 2013-08-01

©2013 by Walter de Gruyter Berlin Boston

This article is distributed under the terms of the Creative Commons Attribution Non-Commercial License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

Articles in the same Issue

  1. Masthead
  2. Masthead
  3. Review
  4. Synthesis and photochromism of aryl(heteroaryl)- and diheteroarylethenes – coumarin derivatives
  5. Preliminary Communications
  6. Fluorescent labeling of oleanolic acid using ‘click’ chemistry
  7. Facile synthetic entry into rotationally restricted 9-arylacridines
  8. Research Articles
  9. Selective fluorescence sensing of ferric ion with novel triazolethione Schiff bases probes
  10. Synthesis and antimicrobial activities of some novel thiophene containing azo compounds
  11. Effect of intramolecular hydrogen bonding on biomimetic reactions by flavins
  12. Synthesis of some novel bis-1,2,4-triazole and bis-1,3,4-thiadiazole derivatives from terephthaloyl and isophthaloyl chlorides
  13. Synthesis of heterocyclic compounds by reaction of dialkyl acetylenedicarboxylates with thiourea derivatives
  14. Synthesis of novel 2-arylsulfonylimino-3,4- dimethyl-5-(5-S-substituted [1,3,4]oxadiazol- 2-yl)-2,3-dihydrothiazole derivatives and their plant growth stimulant activity
  15. Synthesis and biological activity of 6-substituted 5-acetyl-4,7-dimethoxybenzofuran derivatives
  16. Synthesis and biological activity of novel series of heterocyclic compounds containing succinimide moiety
https://doi.org/10.1515/hc-2013-0035
Keywords for this article
thiadiazole; thiosemicarbazide; triazole
Creative Commons
BY-NC-ND 3.0

Articles in the same Issue

  1. Masthead
  2. Masthead
  3. Review
  4. Synthesis and photochromism of aryl(heteroaryl)- and diheteroarylethenes – coumarin derivatives
  5. Preliminary Communications
  6. Fluorescent labeling of oleanolic acid using ‘click’ chemistry
  7. Facile synthetic entry into rotationally restricted 9-arylacridines
  8. Research Articles
  9. Selective fluorescence sensing of ferric ion with novel triazolethione Schiff bases probes
  10. Synthesis and antimicrobial activities of some novel thiophene containing azo compounds
  11. Effect of intramolecular hydrogen bonding on biomimetic reactions by flavins
  12. Synthesis of some novel bis-1,2,4-triazole and bis-1,3,4-thiadiazole derivatives from terephthaloyl and isophthaloyl chlorides
  13. Synthesis of heterocyclic compounds by reaction of dialkyl acetylenedicarboxylates with thiourea derivatives
  14. Synthesis of novel 2-arylsulfonylimino-3,4- dimethyl-5-(5-S-substituted [1,3,4]oxadiazol- 2-yl)-2,3-dihydrothiazole derivatives and their plant growth stimulant activity
  15. Synthesis and biological activity of 6-substituted 5-acetyl-4,7-dimethoxybenzofuran derivatives
  16. Synthesis and biological activity of novel series of heterocyclic compounds containing succinimide moiety
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