Synthesis and reactivity of 4-(2-chloro-5-nitrophenyl)-1,2,3-thiadiazole. A novel one-pot synthesis of N-substituted indole-2-thiols

Journal of Organic Chemistry

Volumn 72, Issue 14, 2007, Pages 5368-5373

  Androsov, Dmitry A ^a   Neckers, Douglas C ^a  

^a BOWLING GREEN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC RINGS; INTERMEDIATES; INTERMOLECULAR CYCLIZATION; THIOKETENE;

ACETIC ACID; AMIDES; CYCLIZATION; ESTERS; NUCLEOPHILES; POTASSIUM COMPOUNDS; RING OPENING POLYMERIZATION; SYNTHESIS (CHEMICAL);

KETONES;

1 BUTY 1,3 DIHYDROPYRROLO[2,3 B]PYRIDINE 2 THIONE; 4 (2 CHLORO 5 NITROPHENYL) 1,2,3 THIADIAZOLE; 4 NITRO 2 (1,2,3 THIADIAZOL 4 YL)BENZENETHIOL; HETEROCYCLIC COMPOUND; INDOLE 2 THIOL DERIVATIVE; THIADIAZOLE DERIVATIVE; THIOACETIC ACID; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; RING OPENING;

INDOLES; MOLECULAR STRUCTURE; NITRO COMPOUNDS; SULFHYDRYL COMPOUNDS; THIAZOLES;

EID: 34447316985     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0707784     Document Type: Article

References (25)

1. Sundberg, R. J. Indoles; Academic Press: London, 1996.
2. Saxton, J. E. Indoles: Wiley-Interscience: New York, 1983.
3. Anderson, M. O.; Shelat, A. A.; Guy, R. K. J. Org. Chem. 2005, 70, 4578-4584.
4. Haramura, M.; Tsuzuki, K.; Okamachi, A.; Yogo, K.; Ikuta, I.; Kozono, T.; Takanashi, H.; Murayama, E. Bioorg. Med. Chem. 2002, 10, 1805-1811.
5. Tokuyama, H.; Watanabe, M.; Hayashi, Y.; Kurokawa, T.; Peng, G.; Fukuyama, T. Synlett 2001, 9, 1403-1406.
6. Wenkerst, E.; Hanna, J. M.; Leftin, M. H.; Michelotti, E. L.; Potts, K. T.; Usifer, D. J. Org. Chem. 1985, 50, 1125-1126.
7. Olgen, S.; Akaho, E.; Nebioglu, D. Farmaco 2005, 60, 497-506.
8. Pedras, M. S. C.; Jha, M. J. Org. Chem. 2005, 70, 1828-1834.
9. Pedras, M. S. C.; Zaharia, I. L. Org. Lett. 2001, 3(8), 1213-1216.
10. Hary, U.; Roettig, U.; Paal, M. Tetrahedron Lett. 2001, 42 5187-5189.
11. Pedras, M. S. C.; Okanga, F. I. J. Agric. Food Chem. 1999, 47, 1196-1202.
12. Pedras, M. S. C.; Khan, A. Q. J. Agric. Food Chem. 1996, 44, 3403-3407.
13. Rewcastle, G. W.; Denny, W. A. Heterocycles 1994, 37(2), 701-708.
14. Rewcastle, G. W.; Palmer, B. D.; Dobrusin, E. M.; Fry, D. W.; Kraker, A. J.; Denny, W. A. J. Med. Chem. 1994, 37(13), 2033-2042.
15. Palmer, B. D.; Rewcastle, G. W.; Thompson, A. M.; Boyd, M.; Showalter, H. D. H.; Sercel, A. D.; Fry, D. W.; Kraker, A. J.; Denny, W. A. J. Med. Chem. 1995, 38(1), 58-67.
16. Wieland, T. Peptides of Poisonous Amanita Mushrooms; Springer-Verlag: New York, 1986.
17. Munekata, E.; Faulstich, H.; Wieland, T. J. Am. Chem. Soc. 1977, 99, 6151-6153.
18. Heber, H.; Faulstich, H.; Wieland, T. Int. J. Pept. Protein Res. 1974, 6, 381-389.
19. Wieland, T.; Miura, T.; Seeliger, A. Int. J. Pept. Protein Res. 1983, 21, 3-10.
20. Adams, A. E.; Pringle, J. R. Methods Enzymol. 1991, 194, 729-731.
21. Butler, R. N.; O'Donoghue, D. A. J. Chem. Soc., Perkin Trans. 1 1982, 5, 1223-1227.
22. Hurd, C. D.; Mori, R. I. J. Am. Chem. Soc. 1955, 77, 5359-5364.
23. Raap, R.; Micetich, R. G. Can. J. Chem. 1968, 46(7), 1057-1063.
24. Mayer, R.; Hunger, B.; Prousa, R.; Muller, A. K. J. Prakt. Chem. 1967, 35(5-6), 294-301.
25. Shafiee, A.; Lalezari, I. J. Heterocycl. Chem. 1973, 10(1), 11-14.