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Volumn 2, Issue 7, 2005, Pages 599-601

New synthesis of pyrazolyl-1,3,4-oxadiazole and 1,3,4-oxadiazoline derivatives

Author keywords

Pyrazolyl 1,3,4 oxadiazoles; Pyrazolyl 1,3,4 oxadiazolines

Indexed keywords

EID: 39049092070 PISSN: 15701786 EISSN: None Source Type: Journal
DOI: 10.2174/157017805774296966 Document Type: Review

Times cited : (5)

References (18)

1
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- Rostom, S. A. F.; Shahaby, M. A. F.; El Demellawy, M. A. Eur. J. Med. Chem. 2003, 38, 959.
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- Rostom, S.A.F.¹ Shahaby, M.A.F.² El Demellawy, M.A.³

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- Abadi, A. H.; Feissa, A. A. H., Hassan, G. S. Chem. Pharm. Bull. 2003, 51, 838.
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- Abadi, A.H.¹ Feissa, A.A.H.² Hassan, G.S.³

3
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- (a) Cottineau, B.; Chenault, J. Synlett,2002, 769.
- (2002) Synlett , pp. 769
- Cottineau, B.¹ Chenault, J.²

4
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- (b) Cottineau, B.; Toto, P.; Marot, C.; Pipaud, A., Chenault, J. Bioorg. Med. Chem. Lett., 2002,12, 2105
- (2002) Bioorg. Med. Chem. Lett , vol.12 , pp. 2105
- Cottineau, B.¹ Toto, P.² Marot, C.³ Pipaud, A.⁴ Chenault, J.⁵

5
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- in press
- (c) Cottineau, B.; Chenault, J.; Guillaumet, G. Tetrahedron Lett., in press.
- Tetrahedron Lett
- Cottineau, B.¹ Chenault, J.² Guillaumet, G.³

7
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- (a) Somoghyi, L. Tetrahedron, 1985, 41, 5190.
- (1985) Tetrahedron , vol.41 , pp. 5190
- Somoghyi, L.¹

8
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- (b) Charisto, D. A.; Vagenas, G. V., Tzavellas, L. C., Tsoleridis, C. A.; Rodios, N. A. J. Heterocyclic Chem., 1994, 31, 1593.
- (1994) J. Heterocyclic Chem , vol.31 , pp. 1593
- Charisto, D.A.¹ Vagenas, G.V.² Tzavellas, L.C.³ Tsoleridis, C.A.⁴ Rodios, N.A.⁵

9
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- (c) Rigo, B.; Couturier, D. J. Heterocyclic Chem., 1986, 23, 253.
- (1986) J. Heterocyclic Chem , vol.23 , pp. 253
- Rigo, B.¹ Couturier, D.²

10
- 46149085070
- Synthesis of compound 3a: To a stirred solution of compound 2 (0.4g, 2.3mmol) in 10ml, of ethanol is added cyanogen bromide (1g, 9.4mmol, The resulting mixture was refluxed during 6h, cooled to rt, neutralized with NaHCO3 and extracted with CH2Cl2. Organic layer was dried over MgSO4 and concentrated under vacuum. Residue was triturated in a mixture of ethyl acetate and acetonitrile and filtered off. Then, filtrate was concentrated under vacuum to give a white solid (230mg, 50, mp: 210°C. 1H NMR (250 MHz, CDCl3) δ 3.75 (3H, s, 3.87 (3H, s) 6.98 (2H, s, 8.02 (1H, s, 13C NMR (63 MHz, CDCl3) δ 39.7; 56.5; 91.7; 132.1; 152.2; 159.6; 163.0. MS: 196 [M+H, IR (KBr) 1628, 1672cm-1
- -1.

11
- 46149122905
- Synthesis of compound 3b: To a stirred solution of compound 2 (0.4g, 2.3mmol) in 5mL of DMF, is added acetic anhydride (2.2mL, 23mmol, The resulting mixture was stirred 24h at rt and concentrated under vacuum. The residue was triturated with a mixture of ethanol and isopropylether (9/1) and filtered off. The resulting solid was added to a solution of P2O5 (0.9g, 6.3mmol) in 4.5mL of MeSO3H, the reaction mixture was stirred at 80°C during 5h, cooled and neutralized with Na2CO3. After extraction with CH2Cl2, the organic layer was separated, dried over MgSO4 and concentrated under vacuum to give a white solid (260mg, 74, mp: 170°C. 1H NMR (250 MHz, CDCl3) δ 2.53 (3H, s, 3.78 (3H, s, 4.00 (3H, s, 7.70 (1H, s, 13C NMR (63 MHz, CDCl3) δ 11.0, 39.5; 56.8; 92.2; 125.9; 131.7; 160.81 162.0. MS: 95 [M+H, IR KBr
- -1.

12
- 46149127489
- Synthesis of compound 3c: To 25ml of acetic anhydride is added slowly, at 0°C, 10mL of formic acid, the resulting solution was warmed to 0°C during 30min and cooled to 0°C. Pyrazole 2 (3g, 14.6mmol) was added to the solution and reaction mixture was refluxed during 5h. After concentration under vacuum. K2CO3 solution and CH2Cl2 were added to the residue, the organic layer was separated, dried over MgSO4 and concentrated under vacuum to give a white solid (1.6g, 50, mp: 216°C. 1H NMR (250 MHz, CDCl3) δ 3.78 (3H, s, 4.00 (3H, s, 7.77 (1 H, s, 8.30 (1H, s, 13C NMR (63 MHz CDCl3) δ 39.9; 57.2; 98.3, 132.5; 151.6; 1589; 160.0 MS: 181 [M+H, IR (KBr) 1672cm-1
- -1.

14
- 4043146093
- Yale, H. L., Losee, K., Martins, J.; Holsing, M.; Perry, F. M., Bernstein, J. J. Am. Chem. Soc., 1953,75, 1933.
- (1953) J. Am. Chem. Soc , vol.75 , pp. 1933
- Yale, H.L.¹ Losee, K.² Martins, J.³ Holsing, M.⁴ Perry, F.M.⁵ Bernstein, J.⁶

15
- 46149083400
- Synthesis of compound 4a: A solution of compound 2 (2g, 11.2mmol) in 30mL of acetone is refluxed during 6h. After cooling to 0°C, the precipitate was filtered off to give a white solid (2.4, 99%). Synthesis of compounds 4b-e, general procedure: A solution of compound 2 (1 g, 5.9mmol) and the carbonyl derivative (11.8mmol) in 30mL of a mixture of ethanol and water (1/2) is refluxed during 8h. After concentration under vacuum, the residue was triturated with ether and filtered off to give a white solid.
- (a) Synthesis of compound 4a: A solution of compound 2 (2g, 11.2mmol) in 30mL of acetone is refluxed during 6h. After cooling to 0°C, the precipitate was filtered off to give a white solid (2.4, 99%). Synthesis of compounds 4b-e, general procedure: A solution of compound 2 (1 g, 5.9mmol) and the carbonyl derivative (11.8mmol) in 30mL of a mixture of ethanol and water (1/2) is refluxed during 8h. After concentration under vacuum, the residue was triturated with ether and filtered off to give a white solid.

16
- 46149108268
- Spectral data for compounds 4a-4e. 4a mp: 152°C. 1H NMR (250 MHz, CDCl3) δ 1.95 (3H, s, 2.15 (3H, s, 3.75 (3H, s, 4.05 (3H, s, 7.85 (1H, s, 9.55 (IH, s, 13 C NMR (63 MHz, CDCl3) δ 16.8; 25.8,39.9; 57.5; 101.9; 135.6; 153.3 158.6; 160.0. MS: 211 [M+H, IR (KBr) 1671, 3343cm-1 4b mp: 195°C. 1H NMR (250 MHz, CDCl3) δ 1.33 (3H, t, J=7.2 Hz, 2.10 (3H, s, 3.75 (3H, s, 4.04 (3H, s, 4.29 (2H, q, J=7,2 Hz, 7.86 (1H, s, 9.78 (1H, s, 13C NMR (63 MHz, CDCl3) δ 11.9; 14.6; 40.0; 57.7; 62.4; 105.6; 107.6; 136.1; 157.0; 165.2, 169.0. MS: 269 [M+H, IR (KBr) 1650, 1696, 3326cm-1. 4c mp: 155°C. 1H NMR (250 MHz, CDCl3) δ 3.72 (3H, s, 4.03 (3H, s, 7.28-7.35 (3H, m, 7.70-7.74 (2H, m, 7.82 (1H, s, 8.10 (1H, s, 9.67 (1H, s, 13C NMR 63 MHz, CDCl
- -1.

17
- 46149118794
- Synthesis of compounds 5a-e, general procedure: A solution of compound 4 (2.4mmol) in 5mL of acetic anhydride is refluxed during 6h. After concentration under vacuum, the residue was purified by flash chromatography on silica gel to give a white solid.
- (a) Synthesis of compounds 5a-e, general procedure: A solution of compound 4 (2.4mmol) in 5mL of acetic anhydride is refluxed during 6h. After concentration under vacuum, the residue was purified by flash chromatography on silica gel to give a white solid.

18
- 46149124005
- Spectral data for compounds 5a-e. 5a mp: 128°C. 1H NMR (250 MHz, CDCl3) δ 1.77 (6H, s) 2.25 (3H, s, 3.74 (3H, s, 3.97 (3H, s, 7.49 (1H, s, 13 C NMR (63 MHz, CDCl3) δ 22.8, 24.9; 31.4; 39.8; 57.2; 99.1; 132.7; 149.8; 161.0; 166.5. MS: 253 [M+H, IR (KBr) 1638cm-1.5b mp: 98°C. 1H NMR (250 MHz, CDCl3) 1.20 (3H, t, J=7,0 Hz, 1.83 (3H, s, 2.24 (3H, s, 3.71 (3H, s, 3.95 (3H, s, 4.18 (2H, q, J=7,0 Hz, 7.48 (1H, s, 13C NMR (63 MHz, CDCl3) δ 12.9; 19.3; 20.4; 38.4; 55.7; 61.4; 90.8; 93.4; 131.4; 148.2; 159.9; 165.1; 166.1. MS: 311 [M+H, IR (KBr) 1659, 1744cm-1. 5c mp: 149°C. 1H NMR (250 MHz, CDCl3) δ 2.30 (3H, s, 3.72 (3H, s, 3.98 (3H, s, 6.91 (1H, s, 7.32-7.44 (5H, m, 7,52 (1H, s, 13C NMR (63 MHz, CDCl3) δ 22.7; 40.7; 58.1; 9
- -1.

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