5-Furan-2yl[1,3,4]oxadiazole-2-thiol, 5-Furan-2yl-4H [1,2,4] triazole-3-thiol and Their Thiol-Thione Tautomerism
Abstract
:Introduction
Results and Discussion
Experimental
General
General Procedure for the Preparation of IIa,b.
General Procedure for the Preparation of IIIa-g.
Comp. No. | R | X | Yield, % | mp, ºC | IR spectrum, υ, cm-1 | 1H NMR spectrum, δ, ppm (J, Hz) | |||
---|---|---|---|---|---|---|---|---|---|
IIa | O | 45 | 161 | 2982 (CH),1636(C=N), 1260(C=S). | 6.60-7.60 (m, 3H, furyl), 2.10 (s, 3H, SCH3) | ||||
IIb | NH | 50 | 132 | 3130(NH), 2982(CH), 1636(C=N),1260(C=S). | 6.60-7.50 (m, 3H, furyl), 5.70 (1H, NH), 2.10 (s, 3H, SCH3 | ||||
IIIa | | O | 82 | 133 | 2990(CH),1632(C=N) 1270(C=S). | 6.56-7.60 (m, 3H, furyl), 5.0 (s, 2H, N-CH2-N) 3.70-3.50 (m, 4H, CH2-O-CH2), 2.70-2.60 (m, CH2-N-CH2). | |||
IIIb | | O | 60 | 145 | 3320(NH),2970(CH),1630(C=N),1268(C=S). | 8.24-7.60 (m, 4H, Ar.CH), 6.50-7.60 (m, 3H, furyl), 5.50 (br, 1H, N-CH2-NH), 5.90 (d, J=7 2H, N-CH2-NH), 2.15 (s, 3H, CH3). | |||
IIIc | | O | 62 | 148 | 3315(NH),2970(CH),1630(C=N),1268(C=S). | 8.40-7.80 (m, 4H, Ar.CH), 6.50-7.60 (m, 3H, furyl), 5.50 (br, 1H, N-CH2-NH), 5.90 (d, J=7 2H, N-CH2-NH), 3.70 (s, 3H, OCH3). | |||
IIId | | O | 50 | 193 | 3330(NH), 2982(CH), 1636(C=N),1280(C=S). | 8.20-7.80 (m, 7H, Ar.CH), 6.50-7.60 (m, 3H, furyl), 5.52 (br, 1H, N-CH2-NH), 5.85 (d, J=7 2H, N-CH2-NH). | |||
IIIe | | O | 40 | 128 | 3323(NH), 2982(CH), 1636(C=N),1260(C=S). | 8.25-7.90 (m, 5H, Ar.CH), 6.50-7.60 (m, 3H, furyl), 5.52 (br, 2H, -NH), 5.92 (d, J=7 2H, N-CH2-NH), 3.80 (d, J=9 Ar-CH2-NH). | |||
IIIf | | O | 70 | 133 | 2982(CH),1636(C=N),1265(C=S). | 6.50-7.60 (m, 3H, furyl), 5.80 (s, 2H, N-CH2), 2.10-2.80 (m, 10H, CH2). | |||
IIIg | | O | 35 | 174 | 3315(NH), 2982(CH), 1636(C=N),1270(C=S). | 8.40-7.80 (m, 4H, Ar.CH), 6.50-7.60 (m, 3H, furyl), 5.50 (br, 1H, N-CH2-NH), 6.05 (d, J=7 2H, N-CH2-NH). | |||
Comp No. | Found, % | Formula | Calculated,% | ||||||
C | H | N | S | C | H | N | S | ||
IIa | 46.15 | 3.29 | 15.33 | 17.58 | C7H6N2O2S | 46.15 | 3.32 | 15.37 | 17.60 |
IIb | 46.38 | 3.87 | 23.11 | 17.65 | C7H7N3OS | 46.40 | 3.89 | 23.19 | 17.69 |
IIIa | 49.41 | 4.89 | 15.72 | 11.98 | C11H13N3O3S | 49.43 | 4.90 | 15.72 | 12.00 |
IIIb | 58.49 | 4.54 | 14.60 | 11.13 | C14H13N3O2S | 58.52 | 4.56 | 14.62 | 11.16 |
IIIc | 55.45 | 4.32 | 13.83 | 10.55 | C14H13N3O3S | 55.43 | 4.32 | 13.85 | 10.57 |
IIId | 63.13 | 3.99 | 13.00 | 10.00 | C17H13N3O2S | 63.14 | 4.05 | 12.99 | 9.92 |
IIIe | 58.48 | 4.55 | 14.60 | 11.13 | C14H13N3O2S | 58.52 | 4.56 | 14.62 | 11.16 |
IIIf | 54.28 | 5.68 | 15.78 | 12.01 | C12H15N3O2S | 54.32 | 5.70 | 15.84 | 12.08 |
IIIg | 48.98 | 3.15 | 17.59 | 10.10 | C13H10N4O4S | 49.05 | 3.17 | 17.60 | 10.07 |
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Koparır, M.; Çetin, A.; Cansız, A. 5-Furan-2yl[1,3,4]oxadiazole-2-thiol, 5-Furan-2yl-4H [1,2,4] triazole-3-thiol and Their Thiol-Thione Tautomerism. Molecules 2005, 10, 475-480. https://doi.org/10.3390/10020475
Koparır M, Çetin A, Cansız A. 5-Furan-2yl[1,3,4]oxadiazole-2-thiol, 5-Furan-2yl-4H [1,2,4] triazole-3-thiol and Their Thiol-Thione Tautomerism. Molecules. 2005; 10(2):475-480. https://doi.org/10.3390/10020475
Chicago/Turabian StyleKoparır, M., A. Çetin, and A. Cansız. 2005. "5-Furan-2yl[1,3,4]oxadiazole-2-thiol, 5-Furan-2yl-4H [1,2,4] triazole-3-thiol and Their Thiol-Thione Tautomerism" Molecules 10, no. 2: 475-480. https://doi.org/10.3390/10020475
APA StyleKoparır, M., Çetin, A., & Cansız, A. (2005). 5-Furan-2yl[1,3,4]oxadiazole-2-thiol, 5-Furan-2yl-4H [1,2,4] triazole-3-thiol and Their Thiol-Thione Tautomerism. Molecules, 10(2), 475-480. https://doi.org/10.3390/10020475