Synthesis of 2-mercaptobenzaldehyde, 2-mercaptocyclohex-1- enecarboxaldehydes and 3-mercaptoacrylaldehydes

Chinese Journal of Chemistry

Volumn 30, Issue 10, 2012, Pages 2495-2500

  Niu, Qingfen ^a   Xu, Xiaofeng ^a   Sun, Hongjian ^a   Li, Xiaoyan ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

2 mercaptobenzaldehyde; 2 mercaptocyclohex 1 enecarboxaldehydes; 3 mercaptoacrylaldehydes; aldehyde; Grignard reagent; sulfur

Indexed keywords

EID: 84867795202     PISSN: 1001604X     EISSN: 16147065     Source Type: Journal    
DOI: 10.1002/cjoc.201200433     Document Type: Article

References (41)

1. Schneller, S. W.,. Adv. Heterocycl. Chem., 1975, 18, 59.
2. Katrizky, A. R.,;, Bonlton, A. J.,. Adv. Heterocycl. Chem., 1975, 18, 76.
3. Verma, A. K.,;, Hossain, M. B.,;, Helm, D. V. D.,;, Breitman, T. R.,. J. Med. Chem., 1987, 30, 1474.
4. Lejuene, F.,;, Rivet, J.-M.,;, Gobert, A.,;, Canton, H.,;, Millan, M. J.,. Eur. J. Pharmacol., 1993, 240, 307.
5. Vliet, L. A. V.,;, Rodenhuis, N.,;, Dijkstra, D.,;, Wikstrom, H.,;, Pugsley, T. A.,;, Serpa, K. A.,;, Meltzer, L. T.,;, Heffner, T. G.,;, Wise, L. D.,;, Lajiness, M. E.,;, Huff, R. M.,;, Svensson, K.,;, Sundell, S.,;, Lundmark, M.,. J. Med. Chem., 2000, 43, 2871.
6. Chen, Y.,;, Zhang, Q.,;, Zhang, B.,;, Xia, P.,;, Xia, Y.,;, Yang, Z. Y.,;, Kilgore, N.,;, Wild, C.,;, Morris-Natschka, S. L.,;, Lee, K. H.,. Bioorg. Med. Chem., 2004, 12, 6383.
7. Xia, P.,;, Yin, Z.-J.,;, Chen, Y.,;, Zhang, Q.,;, Zhang, B.,;, Xia, Y.,;, Yang, Z.-Y.,;, Kilgore, N.,;, Wild, C.,;, Morris-Natschke, S. L.,;, Lee, K.-H.,. Bioorg. Med. Chem. Lett., 2004, 14, 3341.
8. Bolognesi, M. L.,;, Bortolini, M.,;, Cavalli, A.,;, Andrisano, V.,;, Rosini, M.,;, Minarini, A.,;, Melchiorre, C.,. J. Med. Chem., 2004, 47, 5945.
9. Spencer, D. J. E.,;, Marr, A. C.,;, Schröder, M.,. Coord. Chem. Rev., 2001, 219-221, 1055.
10. Rogier, D. J. Jr.,;, Carter, J. S.,;, Talley, J. J.,. WO 2001049675 Chem. Abstr., 2001, 135, 107252.
11. Brown, M. J.,;, Carter, P. S.,;, Fenwick, A. E.,;, Fosberry, A. P.,;, Hamprecht, D. W.,;, Hibbs, M. J.,;, Jarvest, R. L.,;, Mensah, L.,;, Milner, P. H.,;, O'Hanlon, P. J.,;, Pope, A. J.,;, Richardson, C. M.,;, West, A.,;, Witty, D. R.,. Bioorg. Med. Chem. Lett., 2002, 12, 3171.
12. Quaglia, W.,;, Pigini, M.,;, Piergentili, A.,;, Giannella, M.,;, Gentili, F.,;, Marucci, G.,;, Carrieri, A.,;, Carotti, A.,;, Poggesi, E.,;, Leonardi, A.,;, Melchiorre, C.,. J. Med. Chem., 2002, 45, 1633.
13. van Vliet, L. A.,;, Rodenhuis, N.,;, Dijkstra, D.,;, Wikstrom, H.,;, Pugsley, T. A.,;, Serpa, K. A.,;, Meltzer, L. T.,;, Heffner, T. G.,;, Wise, L. D.,;, Lajiness, M. E.,;, Huff, R. M.,;, Svensson, K.,;, Sundell, S.,;, Lundmark, M.,. J. Med. Chem., 2000, 43, 2871.
14. Berlin, K. D.,;, Benbrook, D. M.,;, Nelson, E. C.,. US 6586460 Chem. Abstr., 2004, 139, 69392.
15. Terasawa, K.,;, Yokoe, I.,;, Fujisawa, S.,;, Sakagami, H.,. Anticancer Res., 2001, 21, 2629.
16. Dodda, R.,;, Mandal, T.,;, Zhao, C. G.,. Tetrahedron Lett., 2008, 49, 1899.
17. Dodda, R.,;, Goldman, J. J.,;, Mandal, T.,;, Zhao, C. G.,;, Broker, G. A.,;, Tiekinka, E. R. T.,. Adv. Synth. Catal., 2008, 350, 537.
18. Wang, W.,;, Li, H.,;, Wang, J.,;, Zu, L.,. J. Am. Chem. Soc., 2006, 128, 10354.
19. Zu, L.,;, Wang, J.,;, Li, H.,;, Xie, H.,;, Jiang, W.,;, Wang, W.,. J. Am. Chem. Soc., 2007, 129, 1036.
20. Zu, L.,;, Xie, X.,;, Li, H.,;, Wang, J.,;, Jiang, W.,;, Wang, W.,. Adv. Synth. Catal., 2007, 349, 1882.
21. Klein, H.-F.,;, Dala, A.,;, Junga, T.,;, Fl?rkeb, U.,;, Hauptb, H. J.,. Eur. J. Inorg. Chem., 1998, 2027.
22. Gomes, L.,;, Pereira, E.,;, Castro, B.,. J. Chem. Soc., Dalton Trans., 2000, 1373.
23. Klein, H.-F.,;, Bickelhaupt, A.,;, Jung, T.,;, Cordier, G.,. Organometallics, 1994, 13, 2557.
24. Li, X. Y.,;, Sun, H. J.,;, Fl?rke, U.,;, Klein, H.-F.,. Organometallics, 2005, 24, 4347.
25. Klein, H.-F.,;, Bickelhaupt, A.,;, Lemke, M.,;, Sun, H. J.,;, Brand, A.,;, Jung, T.,;, Röhr, C.,;, Flörke, U.,;, Haupt, H. J.,. Organometallics, 1997, 16, 668.
26. Klein, H.-F.,;, Li, X. Y.,;, Sun, H. J.,;, Beck, R.,;, Flörke, U.,;, Haupt, H.-J.,. Inorg. Chim. Acta, 2000, 298, 63.
27. Stenson, P. A.,;, Becerra, A. M.,;, Wilson, C.,;, Blake, A. J.,;, McMaster, J.,;, Schöder, M.,. Chem. Commun., 2006, 317.
28. Hirano, M.,;, Osakada, K.,;, Nohira, H.,;, Miyashita, A.,. J. Org. Chem., 2002, 67, 533.
29. Toste, F. D.,;, Lough, A. J.,;, Still, I. W. J.,. Tetrahedron Lett., 1995, 36, 6619.
30. Gallagher, T.,;, Pardoe, D. A.,;, Porter, R. A.,. Tetrahedron Lett., 2000, 41, 5415.
31. Hsiao, C.-N.,;, Bhagavatula, L.,;, Pariza, R. J.,. Synth. Commun., 1990, 20, 1687.
32. Kagano, H.,;, Itsuda, H.,;, Yamashita, K.,;, Yoshida, K., JP 05155881A Chem. Abstr., 1993, 119, 249828.
33. Zhang, X.,;, Wu, F.,;, Yan, X.,;, Luo, M.,;, Deng, N., CN 1861606A Chem. Abstr., 1993, 145, 505344.
34. Korobov, M. S.,;, Nivorozhkin, L. E.,;, Minkin, V. I.,. Zh. Org. Khim., 1973, 9, 1717.
35. Weissenfels, M.,;, Pulst, M.,. J. Prakt. Chem./Chem-Ztg, 1973, 315, 873.
36. Kuchenbeiser, G.,;, Shaffer, A. R.,;, Zingales, N. C.,;, Beck, J. F.,;, Schmidt, J. A. R.,. J. Organomet. Chem., 2011, 696, 179.
37. Zhang, J.-L.,;, Gong, Y.-F.,. Org. Lett., 2011, 13, 176.
38. Stokes, B. J.,;, Vogel, C. V.,;, Urnezis, L. K.,;, Pan, M.,;, Driver, T. G.,. Org. Lett., 2010, 12, 2884.
39. Chakraborty, A.,;, Ray, J. K.,. Synth. Commun., 1995, 25, 1869.
40. Romagnoli, R.,;, Baraldi, P. G.,;, Carrion, M. D.,;, Cara, C. L.,;, Cruz-Lopez, O.,;, Preti, D.,;, Tolomeo, M.,;, Grimaudo, S.,;, Di Cristina, A.,;, Zonta, N.,;, Balzarini, J.,;, Brancale, A.,;, Sarkar, T.,;, Hamel, E.,. Bioorg. Med. Chem., 2008, 16, 5367.
41. Flower, K. R.,;, Howard, V. J.,;, Naguthney, S.,;, Pritchard, R. G.,;, Warren, J. E.,;, McGown, A. T.,. Inorg. Chem., 2002, 41, 1907.