Efficient and novel method for thiocyanation of aromatic and heteroaromatic compounds using bromodimethylsulfonium bromide and ammonium thiocyanate

Synlett

Volumn , Issue 19, 2007, Pages 2952-2956

  Bhalerao, Dinesh S ^a   Akamanchi, Krishnacharya G ^a  

^a UNIVERSITY OF MUMBAI   (India)

Author keywords

Ammonium thiocyanate; Aromatic thiocyanate; Bromodimethylsulfonium bromide; Heteroaromatic thiocyanate; Thiocyanation

Indexed keywords

AMMONIUM THIOCYANIC ACID; AROMATIC COMPOUND; BROMODIMETHYLSULFONIUM BROMIDE; THIOCYANIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL REACTION; CYANATION; SYNTHESIS;

EID: 37349055154     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-992367     Document Type: Article

References (37)

1. See reviews: (a) Wood, J. L. In Organic Reactions, Vol. 3; Wiley: New York, 1967, 240-266.
2. (b) Kelly, T. R.; Kim, M. H.; Certis, A. D. M. J. Org. Chem. 1993, 58, 5855.
3. (a) Toste, F. D.; Laronde, F.; Still, W. J. Tetrahedron Lett. 1995, 36, 2949.
4. (b) Grant, M. S.; Snyder, H. R. J. Am. Chem. Soc. 1960, 82, 2742.
5. Guy, R. G. In The Chemistry of Cyanates and Their Thio Derivatives, Part 2; Patai, S., Ed.; John Wiley and Sons: New York, 1977, Chap. 18, 819-886.
6. (a) Taylor, E. C.; Kienzle, F. Synthesis 1972, 38.
7. (b) Uemura, S.; Onoe, A.; Okazaki, H.; Okano, M. Bull. Chem. Soc. Jpn. 1975, 48, 619.
8. (c) Kita, Y.; Takada, T.; Mihara, S.; Whelan, B. A.; Tohma, H. J. Org. Chem. 1995, 60, 7144.
9. (d) Khazei, A.; Alizadeh, A.; Vaghei, R. G. Molecules 2001, 6, 253.
10. (a) Toste, F. D.; Stefano, V. D.; Still, I. W. J. Synth. Commun. 1995, 25, 1277.
11. (b) Nair, V.; George, T. G.; Nair, L. G.; Panicker, S. B. Tetrahedron Lett. 1999, 40, 1195.
12. (c) Chakrabarty, M.; Sarkar, S. Tetrahedron Lett. 2003, 44, 8131.
13. (d) Yadav, J. S.; Reddy, S. B. V.; Shubashree, S.; Sadashiv, K. Tetrahedron Lett. 2004, 45, 2951.
14. (e) Yadav, J. S.; Reddy, B. V. S.; Krishna, A. D.; Reddy, C. S.; Narsaiah, A. V. Synthesis 2005, 961.
15. (f) Wu, G.; Liu, Q.; Shen, Y.; Wu, W.; Wu, L. Tetrahedron Lett. 2005, 46, 5831.
16. (a) Das, B.; Holla, H.; Srinivas, Y. Tetrahedron Lett. 2007, 48, 61.
17. (b) Khan, A. T.; Ali, M. A.; Goswami, P.; Chaudhari, L. H. J. Org. Chem. 2006, 71, 8961.
18. (c) Chaudhari, L. H. Synlett 2006, 1619.
19. (d) Khan, A. T.; Mondal, E.; Ghosh, S.; Islam, S. Eur. J. Org. Chem. 2004, 2002.
20. (e) Khan, A. T.; Mondal, E.; Borah, B. M.; Ghosh, S. Eur. J. Org. Chem. 2003, 4113.
21. (a) Furukawa, N.; Inoue, T.; Aida, T.; Oae, S. J. Chem. Soc., Chem. Commun. 1973, 212.
22. (b) Olah, G. A.; Vankar, Y. D.; Arvanaghi, M.; Surya Prakash, G. K. Synthesis 1979, 720.
23. (c) Olah, G. A.; Arvanaghi, M.; Vankar, Y. D. Synthesis 1979, 721.
24. (d) Chow, Y. L.; Bakker, B. H. Can. J. Chem. 1982, 60, 2268.
25. (e) Majetich, G.; Hicks, R.; Reister, S. J. Org. Chem. 1997, 62, 4321.
26. Epstein, I. R.; Kustin, K. J. Phys. Chem. 1992, 96, 6326.
27. 7a 81-82°C).
28. -1.
29. Kaji, A. Nippon Kagaku Zasshi 1961, 82, 382;
30. Chem. Abstr. 1962, 56, 10054h.
31. Nelson, M. J.; Pullin, A. D. E. J. Chem. Soc. 1960, 604.
32. Zaboev, S. A.; Kudryavtzev, N. A. J. Gen. Chem. USSR (Engl. Transl.) 1935, 5, 1607;
33. 4.
34. Kissman, H. M.; Tarbell, D. S.; Williams, J. J. Am. Chem. Soc. 1953, 75, 2959.
35. Charris, J.; Monasterios, M.; Dominguez, J.; Infante, W.; Castro, N. D. Heterocycl. Commun. 2002, 8, 275.
36. Jordan, A. D.; Luo, C.; Reitz, A. B. J. Org. Chem. 2003, 68, 8693.
37. Karade, N. N.; Tiwari, G. B.; Shirodkar, S. G.; Dhoot, B. M. Synth. Commun. 2005, 35, 1197.