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Volume 2003
Issue 2
10.3390/M314
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Short Note

3-Phenyl-5-[1-(phenylsulphonyl)-pent-4-yn]-1,2,4-triazine and 3-Phenyl-5-[1-(phenylsulphonyl)-hex-5-yn]-1,2,4-triazine

by
Danuta Branowska
,
Stanislaw Ostrowski
and
Andrzej Rykowski
*
Institute of Chemistry, University of Podlasie, ul. 3 Maja 54, PL-08-110 Siedlce, Poland
*
Author to whom correspondence should be addressed.
Molbank 2003, 2003(2), M314; https://doi.org/10.3390/M314
Submission received: 26 September 2002 / Accepted: 15 November 2002 / Published: 24 March 2003
Versions Notes

As part of ongoing research programme we synthesised the title compounds as valuable intermediates for intramolecular cycloaddition reactions, leading to biologically active heterocycles.
Molbank 2003 m314 i001
In a three-necked round-bottom flask (50 mL), equipped with a thermometer, a solution of 4-pentyn phenyl sulphone (2a) or 5-hexyn phenyl sulphone (2b) (1.0 mmole) [1] in dry THF (6 mL) is cooled to -78°C. To the stirred solution, BuLi (1.5 mmole, 0.94 mL of 1.6 N solution in hexane) was added gradually via syringe in such a rate to keep the temperature below -35°C. The mixture was cooled again to -78°C and a solution of 3-phenyl-1,2,4-triazine-5-carbonitrile [2] (1, 182 mg, 1.0 mmole) in dry THF (10 mL) was added dropwise via syringe during a period ca 10 min. It was stirred for ca 2 h and then allowed to warm to room temperature. To this mixture saturated aqueous NH4Cl solution (20 mL) was added and it was extracted with CH2Cl2 (2 x 20 mL), dried over MgSO4, and evaporated to dryness. Column chromatography purification (silica gel 200-300 mesh, eluent: CHCl3) yielded 190 mg (52.5%) of pure 3-phenyl-5-[1-(phenylsulphonyl)-pent-4-yn]-1,2,4-triazine (3a) as a yellow solid (or 140 mg of 3-phenyl- 5-[1-(phenylsulphonyl)-hex-5-yn]-1,2,4-triazine (3b), 37%).
3-Phenyl-5-[1-(phenylsulphonyl)-pent-4-yn]-1,2,4-triazine (3a): 
M.p. 86-87°C.
IR (KBr, cm-1): 3280 (C≡C-H), 1325 & 1165 (SO2).
1H NMR (CDCl3, 200 MHz): 1.97 (t, J = 2.6 Hz, 1 H, C≡CH), 2.00-2.20 (m, 1 H), 2.34-2.52 (m, 1 H), and 2.55-2.68 (m, 2 H) [2 x CH2], 4.65 (dd, J1 = 9.0 Hz, J2 = 5.5 Hz, 1 H, CH(SO2Ph)), 7.41-7.67 (m, 8 H, H-Ar), 8.21-8.27 (m, 2 H, H-Ar), 9.23 (s, 1 H, H-triazine).
MS (EI), m/z (% rel. int.): 363 (2, M+. , 362 (2), 311 (28), 222 (28), 194 (48), 184 (23), 169 (11), 167 (13), 141 (12), 125 (11), 104 (35), 91 (100), 77 (45), 65 (35), 51 (13).
HR-MS (EI) Calcd for C20H17N3SO2: 363.1042; Found: 363.1044.
3-Phenyl-5-[1-(phenylsulphonyl)-hex-5-yn]-1,2,4-triazine (3b): 
M.p. 102-103°C.
IR (KBr, cm-1): 3295 (C≡C-H), 1370 & 1170 (SO2).
1H NMR (CDCl3, 200 MHz) 1.40-1.62 (m, 2 H, CH2), 1.95 (t, J = 2.6 Hz, 1 H, C≡CH), 2.23 (td, J1 = 6.8 Hz, J2 = 2.6 Hz, 2 H, CH2), 2.47-2.61 (m, 2 H, CH2), 4.43 (dd, J1 = 9.9 Hz, J2 = 5.3 Hz, 1 H, CH(SO2Ph)), 7.40-7.66 (m, 8 H, H-Ar), 8.20-8.28 (m, 2 H, H-Ar), 9.26 (s, 1 H, H-triazine).
MS (EI), m/z (% rel. int.): 377 (2, M+. , 376 (4), 311 (11), 208 (40), 105 (100), 104 (34), 103 (29), 79 (33), 77 (48), 65 (11), 51 (9).
HR-MS (EI) Calcd for C21H19N3SO2: 377.1198; Found: 377.1192.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3Supplementary File 4Supplementary File 5Supplementary File 6

References

  1. Prepared from methyl phenyl sulphone and corresponding 4-iodo-1-butyne or 5-iodo-1-pentyne, under argon in dry THF at -78°C to r.t., in presence of BuLi (modified procedure of: Taylor, E.C.; Macor, J.E.; French, L.G. J. Org. Chem. 1991, 56, 1807.).
  2. Huang, J.J. J. Heterocycl. Chem. 1996, 22, 1329.Rykowski, A.; Branowska, D.; Makosza, M.; van Ly, P. J. Heterocycl. Chem. 1996, 33, 1567.

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MDPI and ACS Style

Branowska, D.; Ostrowski, S.; Rykowski, A. 3-Phenyl-5-[1-(phenylsulphonyl)-pent-4-yn]-1,2,4-triazine and 3-Phenyl-5-[1-(phenylsulphonyl)-hex-5-yn]-1,2,4-triazine. Molbank 2003, 2003, M314. https://doi.org/10.3390/M314

AMA Style

Branowska D, Ostrowski S, Rykowski A. 3-Phenyl-5-[1-(phenylsulphonyl)-pent-4-yn]-1,2,4-triazine and 3-Phenyl-5-[1-(phenylsulphonyl)-hex-5-yn]-1,2,4-triazine. Molbank. 2003; 2003(2):M314. https://doi.org/10.3390/M314

Chicago/Turabian Style

Branowska, Danuta, Stanislaw Ostrowski, and Andrzej Rykowski. 2003. "3-Phenyl-5-[1-(phenylsulphonyl)-pent-4-yn]-1,2,4-triazine and 3-Phenyl-5-[1-(phenylsulphonyl)-hex-5-yn]-1,2,4-triazine" Molbank 2003, no. 2: M314. https://doi.org/10.3390/M314

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