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Synthesis of 2-amino-5-mercapto-1,3,4-thiadiazole derivatives

  • Wen-You Li EMAIL logo , Yong Song , Hong-Bo Chen and Wen-Long Yang
Published/Copyright: February 3, 2014
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Heterocyclic Communications
From the journal Heterocyclic Communications Volume 20 Issue 1

Abstract

2-Amino-5-mercapto-1,3,4-thiadiazole (AMT) was used to synthesize 24 new compounds. The structures were confirmed by 1H NMR and 13C NMR.

Keywords: 2-amino-5-mercapto-1,3,4-thiadiazole; chloroacetyl chloride; heterocyclic

Introduction

Recent drug studies are highly focused on heterocyclic ring systems. Thiadiazoles are one of the privileged structural fragments. Fused systems containing the thiadiazole ring give rise to compounds with varied bioactivities, such as anticancer [1], antimicrobial [2, 3], and antiviral [4] properties. Currently, compounds A [5] and B [6, 7] (Figure 1) are in clinical trials, and several other 1,3,4-thiadiazole derivatives including C [8, 9], D [10], and the parent compound 2-amino-5-mercapto-1,3,4-thiadiazole (AMT) [11–15] display a variety of biological activities. Several synthetic strategies to AMT have been reported [16]. The easy accessibility of AMT prompted us to prepare a new series of 2-amino-5-mercapto-1,3,4-thiadiazole derivatives.

Figure 1 Selected biologically active 1,3,4-thiadiazole derivatives.
Figure 1

Selected biologically active 1,3,4-thiadiazole derivatives.

Results and discussion

First, the Michael addition reaction of AMT with α,β-unsaturated compounds was studied. With acrylonitrile as the substrate, the products 1a and 2a were obtained in the respective yields of 47% and 49% under optimal conditions. This reaction was studied using EtOH, acetone, DMSO, water, and MeOH. The results indicated that MeOH is the optimal solvent. The reaction hardly proceeded in the remaining solvents. The highest yields of 1a and 2a were obtained in the presence of triethylamine, lower yields were obtained in the presence of EtONa, and no products were detected in the attempted reactions in the presence of NaOH or NaHCO3. Products 1b,c and 2b,c were prepared in a similar manner by subjecting AMT to the Michael addition with methyl acrylate and butyl acrylate (Scheme 1).

Scheme 1
Scheme 1

Then, our attention focused on the acylation reaction of 1a–c and 2a–c with chloroacetyl chloride, which yielded the respective derivatives 3a–c and 4a–c. These products were cyclized to two different rings by the reaction with potassium isothiocyanate. The imidazole derivatives 5a–c and 7a–c are formed in the reaction with KSCN conducted in acetonitrile, and the thiazole derivatives 6a–c and 8a–c are obtained in DMF at 80°C. A unified mechanism that accounts for these two different outcomes is proposed in Scheme 2.

Scheme 2
Scheme 2

Experimental

General

Melting points were determined on a Perkin-Elmer differential scanning calorimeter and are uncorrected. The IR spectra were run on a Nicolete spectrometer using KBr pellets. NMR spectra were recorded at 400 MHz (1H) and 100 MHz (13C) on a Varian Mercury plus-400 instrument.

General procedure for synthesis of compounds 1a–c and 2a–c

Triethylamine (0.6 mL, 0.86 mmol) was slowly added to a solution of AMT (0.66 g, 5 mmol), acrylonitrile, methyl acrylate or butyl acrylate (2 mmol) in CH3OH (50 mL) under nitrogen, and the mixture was heated under reflux for 4–8 h. After cooling, the mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography eluting with dichloromethane/methanol (95:5) to give starting AMT followed by the products 1a–c and 2a–c.

3-(5-Amino-2-thioxo-1,3,4-thiadiazol-3(2H)-yl)propanenitrile (1a)

Yield 47%; mp 103–105°C; IR (cm-1): 3415, 3284, 2173, 1619, 1553, 1182, 1066; 1H NMR (CDCl3): δ 3.04 (t, J = 7 Hz, 2H), 4.41 (t, J = 7 Hz, 2H), 6.68 (s, 2H). Anal. Calcd for C5H6N4S2: C, 32.24; H, 3.25; N, 30.08; S, 34.43. Found: C, 32.22; H, 3.26; N, 30.07; S, 34.45.

Methyl 3-(5-amino-2-thioxo-1,3,4-thiadiazol-3(2H)-yl)propanoate (1b)

Yield 29%; mp 119–121°C; IR (cm-1): 3416, 3285, 2924, 1718, 1620, 1556, 1213, 1068; 1H NMR (CDCl3): δ 2.82 (t, J = 7 Hz, 2H), 3.64 (s, 3H), 4.36 (t, J = 7 Hz, 2H), 6.60 (s, 2H). Anal. Calcd for C6H9N3O2S2: C, 32.86; H, 4.14; N, 19.16; O, 14.59; S, 29.25. Found: C, 32.88; H, 4.13; N, 19.18; O, 14.57; S, 29.23.

Butyl 3-(5-amino-2-thioxo-1,3,4-thiadiazol-3(2H)-yl)propanoate (1c)

Yield 17%; red brown foam; IR (cm-1): 3315, 3191, 2959, 1724, 1559, 1256, 1184, 1068; 1H NMR (CDCl3): δ 0.92 (t, J = 8 Hz, 3H), 1.41 (m, J = 8 Hz, 2H), 1.61 (m, J = 8 Hz, 2H), 2.83 (t, J = 8 Hz, 2H), 4.07 (t, J = 8 Hz, 2H), 4.37 (t, J = 8 Hz, 2H), 6.55 (s, 2H). Anal. Calcd for C9H15N3O2S2: C, 41.36; H, 5.78; N, 16.08; O, 12.24; S, 24.54. Found: C, 41.37; H, 5.76; N, 16.06; O, 12.23; S, 24.56.

3-[(5-Amino-1,3,4-thiadiazol-2-yl)thio]propanenitrile (2a)

Yield 49%; mp 136–137°C; IR (cm-1): 3297, 3102, 2170, 1631, 1579, 1504, 1068; 1H NMR (CDCl3): δ 2.93 (t, J = 7 Hz, 2H), 3.33 (t, J = 7 Hz, 2H), 7.38 (s, 2H). Anal. Calcd for C5H6N4S2: C, 32.24; H, 3.25; N, 30.08; S, 34.43. Found: C, 32.25; H, 3.27; N, 30.09; S, 34.44.

Methyl 2-[(5-amino-1,3,4-thiadiazol-2-yl)thio]propanoate (2b)

Yield 58%; mp 102–104°C, IR (cm-1): 3311, 3101, 2926, 1728, 1633, 1503, 1246, 1066; 1H NMR (CDCl3): δ 2.81 (t, J = 7 Hz, 2H), 3.34 (t, J = 7 Hz, 2H), 3.65 (s, 3H), 6.64 (s, 2H). Anal. Calcd for C6H9N3O2S2: C, 32.86; H, 4.14; N, 19.16; O, 14.59; S, 29.25. Found: C, 32.85; H, 4.16; N, 19.17; O, 14.60; S, 29.26.

Butyl 2-[(5-amino-1,3,4-thiadiazol-2-yl)thio]propanoate (2c)

Yield 42%; mp 93–95°C, IR (cm-1): 3298, 3102, 2958, 1723, 1502, 1247, 1066; 1H NMR (CDCl3): δ 0.92 (t, J = 7 Hz, 3H), 1.38 (m, J = 7 Hz, 2H), 1.58 (m, J = 7 Hz, 2H), 2.80 (t, J = 7 Hz, 2H), 3.34 (t, J = 7 Hz, 2H), 4.08 (t, J = 7 Hz, 2H), 6.60 (s, 2H). Anal. Calcd for C9H15N3O2S2: C, 41.36; H, 5.78; N, 16.08; O, 12.24; S, 24.54. Found: C, 41.35; H, 5.79; N, 16.07; O, 12.27; S, 24.51.

General procedure for synthesis of compounds 3a–c and 4a–c

Chloroacetyl chloride (2 mmol) was added dropwise to a stirred cold solution (0°C) of 1a–c or 2a–c (1 mmol) in DMF (3 mL) and the mixture was stirred at room temperature for an additional 8 h. After concentration under reduced pressure, the residue was crystallized from ethanol.

2-Chloro-N-(4-(2-cyanoethyl)-5-thioxo-4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamide (3a)

Yield 61%; mp 164–167°C; IR (cm-1): 3439, 2926, 2221, 1712, 1569, 1556, 1079. Anal. Calcd for C7H7ClN4OS2: C, 32.00; H, 2.69; Cl, 13.49; N, 21.32; O, 6.09; S, 24.41. Found: C, 32.02; H, 2.70; Cl, 13.50; N, 21.33; O, 6.08; S, 24.42.

Methyl 3-(5-(2-chloroacetamido)-2-thioxo-1,3,4-thiadiazol-3(2H)-yl)propanoate(3b)

Yield: 88%; mp 112–116°C, IR (cm-1): 3441, 2917, 1710, 1691, 1582, 1212, 1183, 1075. Anal. Calcd for C8H10ClN3O3S2: C, 32.49; H, 3.41; Cl, 11.99; N, 14.21; O, 16.23; S, 21.68. Found: C, 32.50; H, 3.43; Cl, 11.97; N, 14.20; O, 16.25; S, 21.69.

Butyl 3-(5-(2-chloroacetamido)-2-thioxo-1,3,4-thiadiazol-3(2H)-yl)propanoate (3c)

Yield 87%; mp 92–94°C, IR (cm-1): 3432, 2929, 1729, 1709, 1579, 1213, 1184, 1080. Anal. Calcd for C11H16ClN3O3S2: C, 39.11; H, 4.77; Cl, 10.49; N, 12.44; O, 14.21; S, 18.98. Found: C, 39.13; H, 4.75; Cl, 10.50; N, 12.42; O, 14.23; S, 19.00.

2-Chloro-N-[5-((2-cyanoethyl)thio)-1,3,4-thiadiazol-2-yl]acetamide (4a)

Yield 91%; mp 174–178°C, IR (cm-1): 3439, 2925, 2230, 1707, 1582, 1065. Anal. Calcd for C7H7ClN4OS2: C, 32.00; H, 2.69; Cl, 13.49; N, 21.32; O, 6.09; S, 24.41. Found: C, 31.98; H, 2.67; Cl, 13.51; N, 21.30; O, 6.10; S, 24.43.

Methyl 3-[(5-(2-chloroacetamido)-1,3,4-thiadiazol-2-yl)thio]propanoate(4b)

Yield 93%; mp 144–145°C, IR (cm-1): 3439, 2946, 1734, 1706, 1587, 1197, 1177, 1069. Anal. Calcd for C8H10ClN3O3S2: C, 32.49; H, 3.41; Cl, 11.99; N, 14.21; O, 16.23; S, 21.68. Found: C, 32.47; H, 3.43; Cl, 12.01; N, 14.23; O, 16.21; S, 21.67.

Butyl 3-((5-(2-chloroacetamido)-1,3,4-thiadiazol-2-yl)thio)propanoate (4c)

Yield 83%; mp 105–106°C, IR (cm-1): 3435, 2961, 1729, 1704, 1577, 1296, 1183, 1065. Anal. Calcd for C11H16ClN3O3S2: C, 39.11; H, 4.77; Cl, 10.49; N, 12.44; O, 14.21; S, 18.98. Found: C, 39.10; H, 4.79; Cl, 10.51; N, 12.42; O, 14.20; S, 18.97.

General procedure for synthesis of compounds 5a–c and 7a–c

A solution of 3a–c or 4a–c (1 mmol) in acetonitrile (3 mL) was treated with tetrabutylammonium bromide (TBAB, 0.1 g) and KI (0.11 g, 0.66 mmol) and the mixture was stirred for 15 min at room temperature. After addition of KSCN (0.1 g, 1 mmol), the mixture was heated to 80°C for 1 h, then cooled and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with dichloromethane/methanol (95:5).

3-[5-(5-Oxo-2-thioxoimidazolidin-1-yl)-2-thioxo-1,3,4-thiadiazol-3(2H)-yl]propanenitrile (5a)

Yield 56%; mp 162°C, IR (cm-1): 3432, 2273, 1749, 1625, 1571, 1175, 1083; 1H NMR (CDCl3): δ 3.16 (t, J = 7 Hz, 2H), 4.18 (s, 2H), 4.61 (t, J = 7 Hz, 2H), 11.05 (s, 1H). Anal. Calcd for C8H7N5OS3: C, 33.67; H, 2.47; N, 24.54; O, 5.61; S, 33.71. Found: C, 33.69; H, 2.45; N, 24.51; O, 5.63; S, 33.68.

Methyl 3-[5-(5-oxo-2-thioxoimidazolidin-1-yl)-2-thioxo-1,3,4-thiadiazol-3(2H)-yl]propanoate (5b)

Yield 50%; mp 103–104°C, IR (cm-1): 3420, 2922, 1738, 1582, 1251, 1184, 1078; 1H NMR (CDCl3): δ 2.95 (t, J = 7 Hz, 2H), 3.67 (s, 3H), 4.16 (s, 2H), 4.52 (t, J = 7 Hz, 2H), 10.91 (s, 1H). Anal. Calcd for C9H10N4O3S3: C, 33.95; H, 3.17; N, 17.60; O, 15.08; S, 30.21. Found: C, 33.94; H, 3.19; N, 17.59; O, 15.10; S, 30.23.

Butyl 3-[5-(5-oxo-2-thioxoimidazolidin-1-yl)-2-thioxo-1,3,4-thiadiazol-3(2H)-yl]propanoate (5c)

Yield 43%; mp 132–134°C, IR (cm-1): 3429, 2957, 1748, 1633, 1589, 1266, 1179, 1084; 1H NMR (400 MHz, CDCl3): δ 0.93 (t, J = 7 Hz, 3H), 1.40 (m, J = 7 Hz, 2H), 1.60 (m, J = 7 Hz, 2H), 2.95 (t, J =7 Hz, 2H), 4.07 (t, J = 7 Hz, 2H), 4.10 (s, 2H), 4.52 (t, J = 7 Hz, 2H), 11.00 (s, 1H). Anal. Calcd for C12H16N4O3S3: C, 39.98; H, 4.47; N, 15.54; O, 13.32; S, 26.69. Found: C, 39.95; H, 4.49; N, 15.55; O, 13.30; S, 26.70.

3-[(5-(5-Oxo-2-thioxoimidazolidin-1-yl)-1,3,4-thiadiazol-2-yl)thio]propanenitrile (7a)

Yield 67%; mp 196–198°C; IR (cm-1): 3451, 2230, 1734, 1569, 1166, 1053; 1H NMR (CDCl3): δ 3.10 (t, J = 7 Hz, 2H), 3.63 (t, J = 7 Hz, 2H), 4.11 (s, 2H), 10.90 (s, 1H). Anal. Calcd for C8H7N5OS3: C, 33.67; H, 2.47; N, 24.54; O, 5.61; S, 33.71. Found: C, 33.68; H, 2.49; N, 24.53; O, 5.60; S, 33.70.

Methyl 3-[(5-(5-oxo-2-thioxoimidazolidin-1-yl)-1,3,4-thiadiazol-2-yl)thio]propanoate (7b)

Yield 75%; mp 165–167°C, IR (cm-1): 3448, 2923, 1734, 1595, 1174, 1073; 1H NMR (CDCl3): δ 2.89 (t, J = 7 Hz, 2H), 3.53 (t, J = 7 Hz, 2H), 3.67 (s, 3H), 4.10 (s, 2H), 10.90 (s, 1H). Anal. Calcd for C9H10N4O3S3: C, 33.95; H, 3.17; N, 17.60; O, 15.08; S, 30.21. Found: C, 33.96; H, 3.18; N, 17.61; O, 15.07; S, 30.22.

Butyl 3-[(5-(5-oxo-2-thioxoimidazolidin-1-yl)-1,3,4-thiadiazol-2-yl)thio]propanoate (7c)

Yield 42%; mp 110–113°C, IR (cm-1): 3432, 2961, 1734, 1598, 1259, 1175, 1090; 1H NMR (CDCl3): δ 0.92 (t, J = 7 Hz, 3H), 1.40 (m, J = 7 Hz, 2H), 1.61 (m, J = 7 Hz, 2H), 2.89 (t, J = 7 Hz, 2H), 3.53 (t, J = 7 Hz, 2H), 4.10 (t, J = 7 Hz, 2H), 4.10 (s, 2H), 10.89 (s, 1H). Anal. Calcd for C12H16N4O3S3: C, 39.98; H, 4.47; N, 15.54; O, 13.32; S, 26.69. Found: C, 39.97; H, 4.46; N, 15.57; O, 13.33; S, 26.67.

General procedure for synthesis of compounds 6a–c and 8a–c

A solution of 3a–c or 4a–c (1 mmol) in DMF (2 mL) was treated with KI (0.11 g, 0.66 mmol) and KSCN (0.1 g, 1 mmol) and the mixture was heated to 100°C for 1 h. After cooling and concentration under reduced pressure, the residue was crystallized from 80% aqueous ethanol.

3-[5-((4-Oxothiazolidin-2-ylidene)amino)-2-thioxo-1,3,4-thiadiazol-3(2H)-yl]propanenitrile (6a)

Yield 71%; mp 206–208°C, IR (cm-1): 3437, 2924, 2253, 1747, 1623, 1173, 1082; 1H NMR (DMSO-d6): δ 3.110 (t, J = 6 Hz, 2H), 4.17 (s, 2H), 4.49 (t, J = 6 Hz, 2H), 12.48 (s, 1H). Anal. Calcd for C8H7N5OS3: C, 33.67; H, 2.47; N, 24.54; O, 5.61; S, 33.71. Found: C, 33.66; H, 2.45; N, 24.55; O, 5.59; S, 33.72.

Methyl 3-[5-((4-oxothiazolidin-2-ylidene)amino)-2-thioxo-1,3,4-thiadiazol-3(2H)-yl]propanoate (6b)

Yield 71%; mp 161°C, IR (cm-1): 3432, 2939, 1738, 1581, 1252, 1185, 1079; 1H NMR (DMSO-d6): δ 2.90 (t, J = 7 Hz, 2H), 3.615 (s, 3H), 4.15 (s, 2H), 4.42 (t, J = 7 Hz, 2H), 12.43 (s, 1H). Anal. Calcd for C9H10N4O3S3: C, 33.95; H, 3.17; N, 17.60; O, 15.08; S, 30.21. Found: C, 33.94; H, 3.16; N, 17.64; O, 15.05; S, 30.23.

Butyl 3-[5-((4-oxothiazolidin-2-ylidene)amino)-2-thioxo-1,3,4-thiadiazol-3(2H)-yl]propanoate (6c)

Yield 61%; mp 154–155°C, IR (cm-1): 3432, 2960, 1726, 1634, 1575, 1244, 1181, 1082; 1H NMR (DMSO-d6): δ 0.86 (t, J = 7 Hz, 3H), 1.28 (m, J = 7 Hz, 2H), 1.54 (m, J = 7 Hz, 2H), 2.90 (t, J = 7 Hz, 2H), 4.02 (t, J = 7 Hz, 2H), 4.15 (s, 2H), 4.42 (t, J = 7 Hz, 2H), 12.44 (s, 1H). Anal. Calcd for C12H16N4O3S3: C, 39.98; H, 4.47; N, 15.54; O, 13.32; S, 26.69. Found: C, 39.99; H, 4.45; N, 15.53; O, 13.34; S, 26.68.

3-[(5-((4-Oxothiazolidin-2-ylidene)amino)-1,3,4-thiadiazol-2-yl)thio]propanenitrile (8a)

Yield 63%; mp 208–210°C, IR (cm-1): 3432, 2933, 2245, 1735, 1651, 1561, 1168; 1H NMR (400 MHz, DMSO): δ 3.05 (t, J = 6 Hz, 2H), 3.55 (t, J = 6 Hz, 2H), 4.11 (s, 2H), 12.35 (s, 2H). Anal. Calcd for C8H7N5OS3: C, 33.67; H, 2.47; N, 24.54; O, 5.61; S, 33.71. Found: C, 33.69; H, 2.43; N, 24.57; O, 5.59; S, 33.70.

Methyl 3-[(5-((4-oxothiazolidin-2-ylidene)amino)-1,3,4-thiadiazol-2-yl)thio]propanoate (8b)

Yield 65%; mp 176–177°C, IR (cm-1): 3430, 2924, 1732, 1597, 1251, 1173, 1071; 1H NMR (DMSO-d6): δ 2.85 (t, J = 7 Hz, 2H), 3.45 (t, J = 7 Hz, 2H), 3.63 (s, 3H), 4.11 (s, 2H), 12.33 (s, 1H). Anal. Calcd for C9H10N4O3S3: C, 33.95; H, 3.17; N, 17.60; O, 15.08; S, 30.21. Found: C, 33.97; H, 3.19; N, 17.62; O, 15.07; S, 30.20.

Butyl 3-[(5-((4-oxothiazolidin-2-ylidene)amino)-1,3,4-thiadiazol-2-yl)thio]propanoate (8c)

Yield 72%; mp 111–112°C, IR (cm-1): 3405, 2958, 1732, 1594, 1171, 1248, 1056; 1H NMR (DMSO-d6): δ 0.88 (t, J = 8 Hz, 3H), 1.33 (m, J =8 Hz, H), 1.55 (m, J = 8 Hz, 2H), 2.84 (t, J = 8 Hz, 2H), 3.45 (t, J = 8 Hz, 2H), 4.05 (t, J = 8 Hz, 2H), 4.11 (s, 2H), 12.33 (s, 1H). Anal. Calcd for C12H16N4O3S3: C, 39.98; H, 4.47; N, 15.54; O, 13.32; S, 26.69. Found: C, 40.00; H, 4.46; N, 15.57; O, 13.30; S, 26.70.

Corresponding author: Wen-You Li, Dalian University of Technology, Dalian 116012, P.R. China; and Department of Chemical Engineering, Jiuquan Vocational and Technical College, Jiuquan 735000, P.R. China, e-mail:

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Received: 2013-11-3
Accepted: 2013-11-19
Published Online: 2014-02-03
Published in Print: 2014-02-01

©2014 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.

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https://doi.org/10.1515/hc-2013-0212
Keywords for this article
2-amino-5-mercapto-1,3,4-thiadiazole; chloroacetyl chloride; heterocyclic
Creative Commons
BY-NC-ND 3.0

Articles in the same Issue

  2. Frontmatter
  3. Preliminary Communication
  4. One-pot three-component synthesis of substituted 2-(1,2,3-triazol-1-yl)pyrimidines from pyrimidin-2-yl sulfonates, sodium azide and active methylene ketones
  5. Research Articles
  6. A convenient synthesis of 5,5′-bi-1,2,4-triazines via direct S-arylation and its application in the synthesis of 2,2′-bipyridines
  7. An efficient approach to the key intermediate of rosuvastatin
  8. Synthesis and properties of multifunctional hindered amine light stabilizers
  9. Tertiary formylated amines by microwave irradiation of N,N-dimethyl-N′-(2-pyridyl)formamidines with methyl vinyl ketone
  10. Synthesis and antimicrobial activity of some novel 2-thienyl substituted heterocycles
  11. Synthesis of 2-amino-5-mercapto-1,3,4-thiadiazole derivatives
  12. An easy and efficient protocol for the condensation reaction of isatin and N-substituted isatins with 1,2-diaminobenzene using low cost reusable clay catalyst
  13. Synthesis and antimicrobial activities of novel 6-(1,3-thiazol-4-yl)-1,3-benzoxazol-2(3H)-one derivatives
  14. A concise and efficient synthesis of (+)-preussin
  15. Synthesis, X-ray structural characterization, NLO, MEP, NBO and HOMO-LUMO analysis using DFT study of Zn(II)bis(3,4 dimethoxybenzoate)bis(nicotinamide) dihydrate
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