Synthesis and reactions of 1,10-phenanthroline-2(1H)-thione: a facile synthesis of 2,2′-thiobis-1,10-phenanthroline

Tetrahedron Letters

Volumn 48, Issue 32, 2007, Pages 5593-5595

  Krapcho, A Paul ^a   Sparapani, Silvia ^a   Boxer, Matthew ^a  

^a UNIVERSITY OF VERMONT   (United States)

Author keywords

Heteroaryl substituted sulfides; Phenanthroline thione; Thia bridged phenanthroline pyridine and pyrimidine; Thia bridged phenanthroline

Indexed keywords

1,10 PHENANTHROLINE; 1,10 PHENANTHROLINE 2(1H) THIONE; 1,2 DIBROMOETHANE; 2 CHLORO 1,10 PHENANTHROLINE; 2,2' THIOBIS 1,10 PHENANTHROLINE; ALCOHOL; DIPHENYL ETHER; N,N DIMETHYLFORMAMIDE; POTASSIUM CARBONATE; PYRIMIDINE 1 THIONE; PYRIMIDINE DERIVATIVE; SODIUM SULFATE; THIAZOLE DERIVATIVE; THIOUREA; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; HEATING; PRECIPITATION; SYNTHESIS;

THIA;

EID: 34447264214     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.043     Document Type: Article

References (17)

1. 3) δ 181.0, 149.8, 136.0, 135.9, 135.1, 134.4, 134.1, 128.4, 124.8, 123.8, 123.1, 121.1.
2. Hunziker M., and Hauser U. Heterocycles 19 (1982) 2131 The rather drastic treatment of 1 with KSH in ethanol in a Teflon cup at 140 °C for 24 h led to 2a
3. 2/MeOH (99:1) as the eluent. The fractions were allowed to evaporate to afford beautiful yellow needles of 2a (55 mg, 56%).
4. 2-Chloro-1,10-phenanthroline (1) (1 M equiv) and thiourea (3 M equiv) were refluxed in ethanol for 24 h. The resultant solid was collected by filtration, dissolved in dichloromethane to remove a trace of insoluble substances and concentrated to yield 2a (37%).
5. Moran D., Sukcharoenphon K., Puchta R., Schaefer III H.F., Schleyer v.R., and Hoff C.D. J. Org. Chem. 67 (2002) 9061
6. Chung J.Y.L., Cvetovich R., Tsay F.-H., Dormer P.G., DiMichele L., Mathre D.J., Chilenski J.R., Mao B., and Wenslow R. J. Org. Chem. 68 (2003) 8838
7. Barton D.H.R., Crich D., and Kretzschmar G. J. Chem. Soc., Perkin Trans. 1 (1986) 39
8. Still I.W.J., Plavac N., McKinnon D.M., and Chauhan M.S. Can. J. Chem. 54 (1976) 280
9. 3) δ 161.2, 150.3, 146.0, 145.4, 136.2, 135.7, 129.2, 126.5, 125.9, 125.1, 122.9, 122.0, 13.6.
10. Unpublished observations. Prepared by treatment of 3c with Lawesson's reagent in THF.
11. 6) δ 9.18 (dd, J = 1.6, 4.5 Hz, 1H), 8.67 (d, J = 7.5 Hz, 1H), 8.37 (d, J = 6.5 Hz, 1H), 8.00 (m, 2H), 7.90 (m, 1H), 7.72 (d, J = 8.5 Hz, 1H), 3.76 (t, J = 6.8 Hz, 2H), 3.59 (t, J = 6.8 Hz, 2H), 2.36 (quintet, J = 6.8 Hz, 2H).
12. 6) δ 9.26 (dd, J = 1.4, 4.0 Hz, 1H), 9.03 (d, J = 8.5 Hz, 1H), 8.75 (dd, J = 1.5, 8.0 Hz, 1H), 8.46 (d, J = 9.0 Hz, 1H), 8.31 (m, 2H), 8.01 (dd, J = 4.5, 8.5 Hz, 1H), 6.40 (t, J = 8.7 Hz, 2H), 4.02 (t, J = 8.7 Hz, 2H).
13. 6) HCl salt δ 9.2 (dd, J = 1.5, 5.0 Hz, 2H), 9.0 (d, 8.0 Hz, J = 8.5 Hz, 2H), 8.61 (d, J = 8.5 Hz, 2H), 8.19 (m, 4H), 8.13 (m, 4H).
14. 6) δ 156.8, 150.1, 145.5, 144.6, 137.5, 136.2, 128.8, 126.9, 126.7, 126.2, 124.6, 123.5.
15. Wang W.-J., Sengul A., Luo C.-F., Kao H.-C., and Cheng Y.-H. Tetrahedron Lett. 44 (2003) 7099
16. 6) δ 157.3, 156.0, 150.5, 150.4, 145.8, 144.9, 138.1, 137.6, 136.5, 129.1, 127.0, 126.9, 126.5, 126.2, 124.7, 123.8, 122.8.
17. 6) δ 158.3, 153.8, 150.1, 145.5, 144.8, 137.2, 136.3, 128.7, 128.2, 127.5, 127.4, 126.2, 124.6, 123.5, 118.6.