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Simple and efficient approach to synthesis of [1,2,4]triazolo[4,3-b][1,2,4,6]thiatriazine- 1-oxides from N-triazol-3-ylamidines

  • Azhar Hajri EMAIL logo and Mohamed Lamjed Marzouki
Published/Copyright: March 25, 2017
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Heterocyclic Communications
From the journal Heterocyclic Communications Volume 23 Issue 2

Abstract

A facile method for the synthesis of [1,2,4]triazolo[4,3-b][1,2,4,6]thiatriazine 1-oxides 3a–h is presented. The approach involves a reaction between N-triazol-3-ylamidines 2a–h and thionyl chloride in the presence of pyridine. The structures of the synthesized compounds were confirmed by spectral studies including IR, 1H NMR, 13C NMR, MS and elemental analysis.

Keywords: amidines; iminoester; oxides; synthesis; thiatriazine; thionyl chloride; [1,2,4]triazole

Introduction

1,2,4-Triazoles possess antimicrobial [1], antifungal [2], anti-inflammatory [3], antioxidant [4, 5], antiviral [6], anticancer [7] and anticonvulsant activity [8] depending on the substituents in the ring system. Interestingly, the 1,2,4,6-thiatriazine 1-oxides containing sulfur and nitrogen atoms, demonstrate excellent fungicidal [9] and anti-HIV activities [10]. The aim of the present work is to develop a synthesis of some new heterocyclic compounds [1,2,4]triazolo[4,3-b][1,2,4,6]thiatriazine 1-oxides 3 (Scheme 1).

Scheme 1
Scheme 1

Results and discussion

The synthesis of triazolothiatriazine 1-oxide derivatives 3a–h was carried out according to the two steps outlined in Scheme 1. These products were obtained by treatment of N-triazol-3-ylamidines 2a–h with thionyl chloride in the presence of two equivalents of pyridine in dioxane under reflux. The substrates 2a–h were prepared by reaction of N-triazol-3-yl imidates 1 with a primary amine at room temperature. In turn, the imidates 1 were obtained by condensation of 3-amino[1,2,4]triazole with orthoesters according to a previously reported method [11]. The structures of all synthesized compounds 2a–h and 3a–h are fully consistent with infra-red (IR), 1H NMR, 13C NMR, MS and elemental analysis data. From a mechanistic viewpoint, it can be suggested that intermediate products A are final precursors to the observed products 3a–h. Compounds A could not be isolated because their intramolecular cyclization appears to be fast.

Conclusion

A facile and efficient procedure for the synthesis of novel [1,2,4]triazolo[4,3-b][1,2,4,6]thiatriazine 1-oxides from N-triazol-3-ylamidines and thionyl chloride in the presence of pyridine as a catalyst was developed. The yields ranged from good to excellent.

Experimental

All chemicals, reagents and solvents were obtained from Sigma-Aldrich Company and were used without any purification. The imidate 1 was prepared as previously reported [11].

IR spectra were recorded in KBr pellets with a Nicolet IR200 instrument. 1H NMR (300 MHz) and 13C NMR (75 MHz) spectra were recorded in DMSO-d6 on a Brüker 300 spectrometer. Melting points were determined on an Electrothermal 9100 melting point apparatus. Elemental microanalysis was performed on a model 2400 series II Perkin-Elmer analyzer. The electron-spray ionization (ESI) positive MS spectra were recorded on a Brüker Daltonics LC–MS spectrometer.

General procedure for the synthesis of N-triazol- 3-ylamidines 2a–h

A solution of N-triazol-3-ylimidate (1, 0.2 mol) and primary amine (0.21 mol) in absolute ethanol (20 ml) was stirred at room temperature for 3 days. The resultant precipitate of 2 was collected by filtration and crystallized from methanol.

N-Ethyl-N′-(4H-1,2,4-triazol-3-yl)ethanamidine (2a)

Yield 70%; a white solid; mp 165–167°C; IR: ν 3420 (NHtriazolic), 3130 (NHamidinic), 1645 cm−1 (C=N); 1H NMR: δ 1.56 (t, 3H, J=6.2 Hz, CH3-CH2-NH), 2.14 (s, 3H, CH3-C(N)=N), 3.07 (m, 2H, CH3-CH2-NH-), 7.86 (s, 1H, N=CH-NH), 9.10 (s 1H, CH3-CH2-NH), 10.88 (s, 1H, N=CH-NH); 13C NMR: δ 15.2 (CH3-CH2-NH-), 18.6 (CH3-C(N)=N), 38.7 (CH3-CH2-NH-), 153.8 (N=CH-NH-), 154.3 (N=C(N)-N), 161.5 (N=C(CH3)-N). Anal. Calcd for C6H11N5: C, 47.04; H, 7.24; N, 45.72. Found: C, 47.49; H, 7.25; N, 45.72.

N-Ethyl-N′-(4H-1,2,4-triazol-3-yl)propanamidine (2b)

Yield 80%; a white solid; mp 144–146°C; IR: ν 3445 (NHtriazolic), 3162 (NHamidinic), 1648 cm−1 (C=N); 1H NMR: δ 1.13 (t, 3H, J=6.2 Hz, CH3-CH2-C(NH)=N), 1.44 (t, 3H, J=9.0 Hz, CH3-CH2-NH), 2.62 (q, 2H, J=6.2 Hz, CH3-CH2-C(N)=N), 3.52 (m, 2H, CH3-CH2-NH), 7.66 (s, 1H, N=CH-NH-), 9.60 (s, 1H, CH3-CH2-NH-), 11.08 (s, 1H, N=CH-NH); 13C NMR: δ 9.9 (CH3-CH2-C(N)=N), 14.2 (CH3-CH2-NH), 20.0 (CH3-CH2-C(N)=N), 42.8 (CH3-CH2-NH), 154.6 (N=CH-NH-), 157.0 (N=C(N)N), 167.0 (N=C(CH2CH3)-N). Anal. Calcd for C7H13N5: C, 50.28; H, 7.84; N, 41.88. Found: C, 50.27; H, 7.26; N, 41.89.

N-Propyl-N′-(4H-1,2,4-triazol-3-yl)ethanamidine (2c)

Yield 65%; a white solid; mp 130–132°C ; IR: ν 3440 (NHtriazolic), 3200 (NHamidinic), 1640 cm−1 (C=N); 1H NMR: δ 1.15 (t, 3H, J=8.0 Hz, CH3-CH2-CH2-NH), 2.01 (m, 2H, CH3-CH2-CH2-NH), 2.44 (s, 3H, CH3-C(N)=N), 3.49 (m, 2H, CH3-CH2-CH2-NH), 7.26 (s, 1H, N=CH-NH), 9.72 (s, 1H, CH3-CH2-CH2-NH), 11.80 (s, 1H, N=CH-NH); 13C NMR: δ 12.8 (CH3-CH2-CH2-NH), 22.0 (CH3-CH2-CH2-NH), 23.0 (CH3-C(N)=N), 44.7 (CH3-CH2-CH2-NH), 152.9 (N=CH-NH), 158.6 (N=C(N)-N), 166.6 (N=C(CH3)-N). Anal. Calcd for C7H13N5: C, 50.28; H, 7.84; N, 41.88. Found: C, 50.30 H, 7.85; N, 41.90.

N-Propyl-N′-(4H-1,2,4-triazol-3-yl)propanamidine (2d)

Yield 71%; a white solid; mp 170–172°C; IR: ν 3410 (NHcyclic), 3180 (NHamidinic), 1640 cm−1 (C=N); 1H NMR: δ 1.14 (t, 3H, J=8.2 Hz, CH3-CH2-CH2-NH), 1.31 (t, 3H, J=7.6 Hz, CH3-CH2-C(N)=N), 1.98 (m, 2H, CH3-CH2-CH2-NH), 2.80 (q, 2H, J=7.6 Hz, CH3-CH2-C(N)=N), 3.50 (m, 2H, CH3-CH2-CH2-NH), 7.29 (s, 1H, N=CH-NH), 9.54 (s, 1H, CH3-CH2-CH2-NH), 11.04 (s, 1H, N=CH-NH); 13C NMR: δ 11.6 (CH3-CH2-CH2-NH), 12.9 (CH3-CH2-C(N)=N), 23.0 (CH3-CH2-CH2-NH), 24.0 (CH3-CH2-C(N)=N), 45.9 (CH3-CH2-CH2-NH), 152.8 (N=CH-NH), 156.9 (N=C(N)-N), 165.7 (N=C(CH2CH3)-N). Anal. Calcd for C8H15N5: C, 53.02; H, 8.34; N, 38.64. Found: C, 53.02; H, 8.35; N, 38.63.

N-Cyclopentyl-N′-(4H-1,2,4-triazol-3-yl)ethanamidine (2e)

Yield 63%; mp 185–186°C; IR: ν 3430 (NHtriazolic), 3170 (NHamidinic), 1642 cm−1 (C=N); 1H NMR: δ 1.26 (m, 4H, CH2-CH2-CH2-CH2-CH-NH), 2.40 (s, 3H, CH3-C(N)=N), 2.87 (m, 4H, CH2-CH2-CH2-CH2-CH-NH), 4.49 (m, 1H, CH2-CH2-CH2-CH2-CH-NH), 6.98 (s, 1H, N=CH-NH), 9.41 (s, 1H, CH2-CH2-CH2-CH2-CH-NH), 12.08 (s, 1H, N=CH-NH); 13C NMR: δ 22.9 (CH3-C(N)=N), 23.8 (CH2-CH2-CH2-CH2-CH-N), 33.1 (CH2-CH2-CH2-CH2-CH-NH), 62.6 (CH2-CH2-CH2-CH2-CH-N), 152.8 (N=CH-NH), 155.3 (N=C(N)-N), 165.75 (N=C(CH3)-N). Anal. Calcd for C9H15N5: C, 55.94; H, 7.82; N, 36.24. Found: C, 55.92; H, 7.84; N, 36.25.

N-Cyclopentyl-N′-(4H-1,2,4-triazol-3-yl)propanamidine (2f)

Yield 65%; mp 158–159°C; IR: ν 3438 (NHtriazolic), 3190 (NHamidinic), 1641 cm−1 (C=N); 1H NMR: δ 1.18 (t, J=6.8 Hz, 3H, CH3-CH2-C(N)=N), 1.68 (m, 4H, CH2-CH2-CH2-CH2-CH-NH), 2.80 (m, 4H, CH2-CH2-CH2-CH2-CH-NH), 3.18 (q, 2H, J=6.8 Hz, CH3-CH2-C(N)=N ), 4.43 (m, 1H, CH2-CH2-CH2-CH2-CH-NH), 6.98 (s, 1H, N=CH-NH), 9.22 (s, 1H, CH2-CH2-CH2-CH2-CH-NH), 12.20 (s, 1H, N=CH-NH); 13C NMR: δ 18.0 (CH3-CH2-C(N)=N), 23.6 (CH2-CH2-CH2-CH2-CH-NH), 26.8 (CH3-CH2-C(N)=N), 32.8 (CH2-CH2-CH2-CH2-CH-NH), 63.0 (CH2-CH2-CH2-CH2-CH-NH),152.7 (N=CH-NH), 155.0 (N=C(N)-N), 166.9 (N=C(CH2CH3)-N). Anal. Calcd for C10H17N5: C, 57.95; H, 8.27; N, 33.79. Found: C, 57.96; H, 8.27; N, 33.80.

N-Benzyl-N′-(4H-1,2,4-triazol-3-yl)ethanamidine (2g)

Yield 78%; a white solid, mp 172–174°C, IR: ν 3452 (NHtriazolic), 3185 (NHamidinic), 1643 cm−1 (C=N); 1H NMR: δ 2.33 (s, 3H, CH3-C(N)=N), 4.81 (s, 2H, Ph-CH2-NH), 6.79 (s, 1H, N=CH-NH), 7.40–7.80 (m, 5H, CHaromatic), 9.77 (s, 2H, Ph-CH2-NH), 11.67 (s, 1H, N=CH-NH); 13C NMR: δ 22.0 (CH3-C(N)=N), 49.0 (Ph-CH2-NH), 126.6, 127.8, 132.4, 134.5(Carom,C6H5), 154.0 (N=CH-NH), 157.9 (N=C(N)-N), 166.8 (N=C(CH3)-N). Anal. Calcd for C11H13N5: C, 61.38; H, 6.09; N, 32.45. Found: C, 61.40; H, 6.11; N, 32.45.

N-Benzyl-N′-(4H-1,2,4-triazol-3-yl)propanamidine (2h)

Yield 74%; a white solid; mp 180–182°C, IR: ν 3449 (NHcyclic), 3190 (NHamidinic), 1646 cm−1 (C=N); 1H NMR: δ 1.26 (t, 3H, J=6.2 Hz, CH3-CH2-C(N)=N), 3.32 (q, 2H, J=6.2 Hz, CH3-CH2-C(N)=N), 4.98 (s, 2H, Ph-CH2-NH), 6.99 (s, 1H, N=CH-NH), 7.64-7.88 (m, 5H, CHaromatic), 9.43 (s, 2H, Ph-CH2-NH), 11.92 (s, 1H, N=CH-NH); 13C NMR: δ 11.8 (CH3-CH2-C(N)=N), 27.1 (CH3-CH2-C(N)=N), 50.7 (Ph-CH2-N), 125.2, 126.7, 130.8, 131.1 (Carom,C6H5), 153.6 (N=CH-NH), 159.1 (N=C(N)-N), 166.0 (N=C(CH2CH3)-N); MS: m/z=276 [M+1]+. Anal. Calcd for C12H15N5: C, 62.86; H, 6.59; N, 30.54. Found: C, 62.87; H, 6.60; N, 30.55.

General procedure for synthesis of [1,2,4]triazolo[4,3-b][1,2,4,6]thiatriazine 1-oxides 3a–h

Thionyl chloride (0.12 mol) was added dropwise to a mixture of N-triazol-3-ylamidine 2a–h (0.12 mmol) and pyridine (0.24 mol) in anhydrous 1,4-dioxane (40 ml). The mixture was heated under reflux for 6 h and then left to cool. The precipitate of pyridinium chloride was filtered. The solvent was removed under reduced pressure and the resulting solid was filtered off and crystallized from a mixture of dichloromethane and ethanol (v/v, 8:2) to give an analytically pure product 3a–h.

2-Ethyl-3-methyl-2H-[1,2,4]triazolo[4,3-b][1,2,4,6]thiatriazine 1-oxide (3a)

Yield 52%; a yellow solid; mp 240–242°C, IR: ν 1080 (S=O), 1612 cm−1 (C=N); 1H NMR: δ 1.40 (t, 3H, J=9.0 Hz, CH3-CH2-N), 2.54 (s, 3H, CH3-C(N)=N), 3.47 (q, 2H, J=9.0 Hz, CH3-CH2-N), 7.52 (s, 1H, N=CH-N-SO); 13C NMR: δ 14.2 (CH3-CH2-N), 19.3 (CH3-C(N)=N), 40.3 (CH3-CH2-N), 151.4 (N=CH-N-SO), 156.2 (N=C(N)-N),163.8 (N=C(CH3)-N); ESI-MS : m/z 200 [M+1]+. Anal. Calcd for C6H9N5OS: C, 36.17; H, 4.55; N, 35.15; O, 8.03; S, 16.09. Found: C, 36.18; H, 4.56; N, 35.17; O, 8.04; S, 16.10.

2,3-Diethyl-2H-[1,2,4]triazolo[4,3-b][1,2,4,6]thiatriazine 1-oxide (3b)

Yield 45%; a yellow solid; mp 230–233°C; IR: ν 1080 (S=O), 1612 cm−1 (C=N); 1H NMR: δ 1.06 (t, 3H, J=6.0 Hz, CH3-CH2-C(N)=N), 1.42 (t, 3H, J=9.0 Hz, CH3-CH2-N), 2.58 (q, 2H, J=6.0 Hz, CH3-CH2-C(N)=N), 3.49 (q, 2H, J=9.0 Hz, CH3-CH2-N), 7.66 (s, 1H, N=CH-N-SO); 13C NMR: δ 10.7 (CH3-CH2-C(N)=N), 15.0 (CH3-CH2-N), 20.1 (CH3-CH2-C(N)=N), 41.0 (CH3-CH2-N), 152.60 (N=CH-N-SO), 155.8 (N=C(N)N), 165.1 (N=C (CH2CH3) N); ESI-MS: m/z 214 [M+1]+. Anal. Calcd for C7H11N5OS: C, 39.42; H, 5.20; N, 32.84; O, 7.50; S, 15.04. Found: C, 39.44; H, 5.21; N, 32.86, O; 7.51; S, 15.05.

3-Methyl-2-propyl-2H-[1,2,4]triazolo[4,3-b][1,2,4,6]thiatriazine 1-oxide (3c)

Yield 36%; a beige solid; mp 192–194°C; IR: ν 1081 (S=O), 1616 cm−1 (C=N); 1H NMR: δ 1.13 (t, 3H, J=7.2 Hz, CH3-CH2-CH2-N), 1.90 (m, 2H, CH3-CH2-CH2-N), 2.42 (s, 3H, CH3-C(N)=N), 3.46 (t, 2H, J=6.3 Hz, CH3-CH2-CH2-N), 7.20 (s, 1H, N=CH-N-SO); 13C NMR: δ 12.1 (CH3-CH2-CH2-N), 21.1 (CH3-CH2-CH2-N), 22.8 (CH3-C(N)=N), 43.7 (CH3-CH2-CH2-N), 152.3 (N=CH-N-SO), 157.6 (N=C(N)-N), 166.2 (N=C(CH3)-N); ESI-MS: m/z 214 [M+1]+. Anal. Calcd for C7H11N5OS: C, 39.42; H, 5.20; N, 32.84; O, 7.50; S, 15.04. Found: C, 36.43; H, 5.42; N, 32.86; O, 7.05; S, 15.08.

3-Ethyl-2-propyl-2H-[1,2,4]triazolo[4,3-b][1,2,4,6]thiatriazine 1-oxide (3d)

Yield 40%; a beige solid; mp 212–214°C; IR: ν 1083 (S=O), 1616 cm−1 (C=N); 1H NMR: δ 1.10 (t, 3H, J=8.2 Hz, CH3-CH2-CH2-N), 1.28 (t, 3H, J=8.9 Hz, CH3-CH2-C(N)=N), 1.96 (m, 2H, CH3-CH2-CH2-N), 2.80 (q, 2H, J=8.9 Hz, CH3-CH2-C(N)=N), 3.46 (t, 2H, J=8.4 Hz, CH3-CH2-CH2-N), 7.13 (s, 1H, N=CH-N-SO); 13C NMR: δ 11.2 (CH3-CH2-CH2-N), 12.6 (CH3-CH2-C(N)=N), 22.4 (CH3-CH2-CH2-N), 23.2 (CH3-CH2-C(N)=N), 45.7 (CH3-CH2-CH2-N), 152.0 (N=CH-N-SO), 156.5 (N=C(N)-N), 166.8 (N=C(CH2CH3)-N); ESI-MS: m/z 228 [M+1]+. Anal. Calcd for C8H13N5OS: C, 42.28; H, 5.77; N, 30.81; O, 7.04; S, 14.11. Found: C, 42.29; H, 5.78; N, 30.84; O, 7.05; S, 14.10.

2-Cyclopentyl-3-methyl-2H-[1,2,4]triazolo[4,3-b][1,2,4,6]thiatriazine 1-oxide (3e)

Yield 28%; a yellowish solid; mp 216–2018°C; IR: ν 1082 (S=O), 1615 cm−1 (C=N); 1H NMR: δ 1.24 (m, 4H, CH2-CH2-CH2-CH2-CH-N), 2.38 (s, 3H,CH3-C(N)=N), 2.85(m, 4H, CH2-CH2-CH2-CH2-CH N), 4.48 (m, 1H, CH2-CH2-CH2-CH2-CH N), 6.88(s, 1H, N=CH-N-SO); 13C NMR: δ 22.8 (CH3-C(N)=N), 23.6 (CH2-CH2-CH2-CH2-CH-N), 32.2 (CH2-CH2-CH2-CH2-CH-N), 62.0 (CH2-CH2-CH2-CH2-CH-N), 151.8 (N=CH-N-SO), 155.5 (N=C(N)-N), 165.3 (N=C(CH3)-N). ESI-MS : m/z 240 [M+1]+. Anal. Calcd for C9H13N5OS: C, 45.17; H, 5.48; N, 29.27; O, 6.69; S, 13.40. Found: C, 45.18; H, 5.50; N, 29.28; O, 6.71; S, 13.41.

2-Cyclopentyl-3-ethyl-2H-[1,2,4]triazolo[4,3-b][1,2,4,6]thiatriazine 1-oxide (3f)

Yield 25%; a yellowish solid; mp 200–202°C; IR: ν 1080 (S=O), 1616 cm−1 (C=N); 1H NMR: δ 1.16 (t, J=6.4 Hz, 3H, CH3-CH2-C(N)=N), 1.62 (m, 4H, CH2-CH2-CH2-CH2-CH-N), 2.77 (m, 4H, CH2-CH2-CH2-CH2-CH-N), 3.10 (q, 2H, J=6.4 Hz, CH3-CH2-C(N)=N), 4.40 (m, 1H, CH2-CH2-CH2-CH2-CH-N), 6.92 (s, 1H, N=CH-N-SO); 13C NMR: δ 17.0 (CH3-CH2-C(N)=N), 23.0 (CH2-CH2-CH2-CH2-CH-N), 26.2 (CH3-CH2-C(N)=N) 31.9 (CH2-CH2-CH2-CH2-CH-N), 62.8 (CH2-CH2-CH2-CH2-CH-N), 152.5 (N=CH-N-SO), 154.8 (N=C(N)-N), 166.2 (N=C(CH2CH3)-N); ESI-MS: m/z 254 [M+1]+. Anal. Calcd for C10H15N5OS: C, 47.41; H, 5.97; N, 27.65; O, 6.32; S, 12.66. Found: C, 45.18; H, 5.50; N, 29.28; O, 6.71; S, 13.41.

2-Benzyl-3-methyl-2H-[1,2,4]triazolo[4,3-b][1,2,4,6]thiatriazine 1-oxide (3g)

Yield 47%; a brown solid; mp 209–201°C; IR: ν 1080 (S=O), 1614 cm−1 (C=N); 1H NMR: δ 2.30 (s, 3H, CH3-C(N)=N), 4.78 (s, 2H, Ph-CH2-N), 6.70 (s, 1H, N=CH-N-SO), 7.02–7.30 (m, 5H, CHaromatic); 13C NMR: δ 21.2 (CH3-C(N)=N), 48.5 (Ph-CH2-N), 125.6, 126.4, 130.4, 132.02 (Carom,C6H5), 153.0 (N=CH-N-SO), 157.1 (N=C(N)-N), 166.2 (N=C(CH3)-N); ESI-MS: m/z 262 [M+1]+. Anal. Calcd for C11H11N5OS: C, 50.56; H, 4.24; N, 26.80; O, 6.12; S, 12.27. Found: C, 50.57; H, 4.27; N, 26.79; O, 6.10; S, 12.30.

2-Benzyl-3-ethyl-2H-[1,2,4]triazolo[4,3-b][1,2,4,6]thiatriazine 1-oxide (3h)

Yield 50%; a dark brown solid; mp 242–242°C; IR: ν 1083 (S=O), 1614 cm−1 (C=N); 1H NMR: δ 1.23 (t, 3H, J=6.8 Hz, CH3-CH2-C(N)=N), 3.22 (q, 2H, J=6.8 Hz, CH3-CH2-C(N)=N), 4.90 (s, 2H, Ph-CH2-N), 6.75 (s, 1H, N=CH-N-SO), 7.30-7.81 (m, 5H, CHaromatic); 13C NMR: δ 11.2 (CH3-CH2-C(N)=N), 26.0 (CH3-CH2-C(N)=N), 50.01 (Ph-CH2-N), 124.6, 125.9, 129.8, 131.6 (Carom,C6H5), 152.64 (N=CH-N-SO),157.6 (N=C(N)-N), 165.0 (N=C(CH2CH3)-N); ESI-MS: m/z 276 [M+1]+. Anal. Calcd for C12H13N5OS: C, 52.35; H, 4.76; N, 25.44; O, 5.81; S, 11.65. Found: C, 52.36; H, 4.78; N, 25.45; O, 5.82; S, 11.66.

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Received: 2017-1-20
Accepted: 2017-2-3
Published Online: 2017-3-25
Published in Print: 2017-4-1

©2017 Walter de Gruyter GmbH, 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. Frontmatter
  2. Preliminary Communications
  3. Synthesis of 7-cyanoindolizine derivatives via a tandem reaction
  4. A new facile way for the preparation of 3-formylcoumarins
  5. Research Articles
  6. Synthesis and spectral evaluation of 5,10,15,20-tetrakis(3,4-dibenzyloxyphenyl)porphyrin
  7. Stereoselective cascade assembling of benzylidenecyanoacetates and 1,3-dimethylbarbituric acid into (1R*,2S*)-1-cyano-5,7-dialkyl-4,6,8-trioxo-2-aryl-5,7-diazaspiro[2.5]octane-1-carboxylates
  8. Ultrasound mediated synthesis of dihydropyrano[3,2-d][1,3]dioxin-7-carbonitrile derivatives in H2O/EtOH medium
  9. Simple and efficient approach to synthesis of [1,2,4]triazolo[4,3-b][1,2,4,6]thiatriazine- 1-oxides from N-triazol-3-ylamidines
  10. Synthesis of 4H-3-aryl-2-cyano-1,4-benzothiazine 1,1-dioxides for antiviral studies
  11. Design, synthesis and antibacterial evaluation of 2-alkyl- and 2-aryl-3-(phenylamino)quinazolin-4(3H)-one derivatives
  12. Regio- and stereoselective synthesis of [1,3]thiazolo[3,2-b][1,2,4]triazol-7-ium salts via electrophilic heterocyclization of 3-S-propargylthio-4Н-1,2,4-triazoles and their antimicrobial activity
  13. Synthesis, spectroscopic characterization, X-ray structure and DFT calculations of Ni(II)bis(3,4 dimethoxybenzoate)bis(nicotinamide) dihydrate
  14. 13C NMR spectroscopy of heterocycles: 1-phenyl-3-aryl/t-butyl-5-arylpyrazoles
https://doi.org/10.1515/hc-2017-0003
Keywords for this article
amidines; iminoester; oxides; synthesis; thiatriazine; thionyl chloride; [1,2,4]triazole
Creative Commons
BY-NC-ND 3.0

Articles in the same Issue

  1. Frontmatter
  2. Preliminary Communications
  3. Synthesis of 7-cyanoindolizine derivatives via a tandem reaction
  4. A new facile way for the preparation of 3-formylcoumarins
  5. Research Articles
  6. Synthesis and spectral evaluation of 5,10,15,20-tetrakis(3,4-dibenzyloxyphenyl)porphyrin
  7. Stereoselective cascade assembling of benzylidenecyanoacetates and 1,3-dimethylbarbituric acid into (1R*,2S*)-1-cyano-5,7-dialkyl-4,6,8-trioxo-2-aryl-5,7-diazaspiro[2.5]octane-1-carboxylates
  8. Ultrasound mediated synthesis of dihydropyrano[3,2-d][1,3]dioxin-7-carbonitrile derivatives in H2O/EtOH medium
  9. Simple and efficient approach to synthesis of [1,2,4]triazolo[4,3-b][1,2,4,6]thiatriazine- 1-oxides from N-triazol-3-ylamidines
  10. Synthesis of 4H-3-aryl-2-cyano-1,4-benzothiazine 1,1-dioxides for antiviral studies
  11. Design, synthesis and antibacterial evaluation of 2-alkyl- and 2-aryl-3-(phenylamino)quinazolin-4(3H)-one derivatives
  12. Regio- and stereoselective synthesis of [1,3]thiazolo[3,2-b][1,2,4]triazol-7-ium salts via electrophilic heterocyclization of 3-S-propargylthio-4Н-1,2,4-triazoles and their antimicrobial activity
  13. Synthesis, spectroscopic characterization, X-ray structure and DFT calculations of Ni(II)bis(3,4 dimethoxybenzoate)bis(nicotinamide) dihydrate
  14. 13C NMR spectroscopy of heterocycles: 1-phenyl-3-aryl/t-butyl-5-arylpyrazoles
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