Synthesis of highly branched sulfur-nitrogen heterocycles by cascade cycloadditions of [1,2]dithiolo[1,4]thiazines and [1,2]dithiolopyrroles

Journal of Organic Chemistry

Volumn 69, Issue 11, 2004, Pages 3672-3682

  Barriga, Susana ^a   Fuertes, Pedro ^a   Marcos, Carlos F ^b   Torroba, Tomás ^a  

^a UNIVERSITY OF BURGOS   (Spain)

^b UNIVERSITY OF EXTREMADURA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; MOLECULAR STRUCTURE; NITROGEN; SULFUR; SYNTHESIS (CHEMICAL);

HETEROCYCLES;

NITROGEN COMPOUNDS;

1,2 DITHIOLE 3 THIONE DERIVATIVE; 2,3,7,8 TETRABENZOYL 4,6 BIS[SPIRO(4,5 DIBENZOYL 1,3 DITHIOL 2 YL)] 5 ETHYLBISTHIOPYRANO[2,3 B:2',3' E][1,4]THIAZINE; 2,3,7,8 TETRABENZOYL 4,6 BIS[SPIRO(4,5 DIBENZOYL 1,3 DITHIOL 2 YL)] 5 ETHYLBISTHIOPYRANO[2,3 B:2'3' D]PYRROLE; 2,3,7,8 TETRABENZOYL 4,6 BIS[SPIRO(4,5 DIBENZOYL 1,3 DITHIOL 2 YL)] 5 STEARYLBISTHIOPYRANO[2,3 B:2',3' E][1,4]THIAZINE; 3 (4,5 DIBENZOYL 1,3 DITHIOL 2 YLIDENYL) 4 ETHYL 5 SPIRO(4,5 DIBENZOYL 1,3 DITHIOL 2 YL) 6,7 DIBENZOYLTHIOPYRANO[2,3 B][1,4]THIAZINE 6 THIONE; 4 ETHYL 3,5 BIS(4,5 DIBENZOYL 1,3 DITHIOL 2 YLIDENYL)[1,4]THIAZINE 2,6 DITHIONE; ACETYLENE DERIVATIVE; ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; ANTINEOPLASTIC AGENT; BIS[1,2]DITHIOLOPYRROLE DITHIONE; DIBENZOYLACETYLENE; HETEROCYCLIC COMPOUND; HEXAMETHYL 2 THIOXO 3 (1,3 DITHIOL 2 YLIDENYL) 4 ETHYL 5 SPIRO(1,3 DITHIOL 2 YL)THIOPYRANO[2,3 E][1,4]THIAZINE 4',4'',5',5'',6,7 HEXACARBOXYLATE; NITROGEN DERIVATIVE; OCTAMETHYL 4,6 BIS[SPIRO(1,3 DITHIOL 2 YL)] 5 ETHYLBISTHIOPYRANO[2,3 B:2',3' D]PYRROLE 2,3,4',4'',5',5'',7,8 OCTACARBOXYLATE; OCTAMETHYL 4,6 BIS[SPIRO(1,3 DITHIOL 2 YL)] 5 ETHYLBISTHIOPYRANO[2,3 B:2',3' E][1,4]THIAZINE 2,3,4',5',4'',5'',7,8 OCTACARBOXYLATE; OCTAMETHYL 4,6 BIS[SPIRO(1,3 DITHIOL 2 YL)] 5 ETHYLTHIOPYRANO[2,3 B]CYCLOPENTA[D]PYRROLE 2,3,4',4'',5',5'',7,8 OCTACARBOXYLATE; POLYCYCLIC HYDROCARBON; PYRROLE DERIVATIVE; SCANDIUM; SCANDIUM TRIFLATE; SULFUR DERIVATIVE; TETRAMETHYL 4 (2 CHLOROETHYL) 3,5 BIS(1,3 DITHIOL 2 YLIDENYL) 2,6 DITHIOXO[1,4]THIAZINE 4',4'',5',5'' TETRACARBOXYLATE; TETRAMETHYL 4 ETHYL 3,5 BIS(1,3 DITHIOL 2 YLIDENYL) 2,6 DITHIOXO[1,4]THIAZINE 4',4'',5',5'' TETRACARBOXYLATE; TETRAMETHYL 4 STEARYL 3,5 BIS(1,3 DITHIOL 2 YLIDENYL) 2,6 DITHIOXO[1,4]THIAZINE 4',4'',5',5'' TETRACARBOXYLATE; THIAZINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; [1,2]DITHIOLOPYRROLE DERIVATIVE; [1,2]DITHIOLO[1,4]THIAZINE DERIVATIVE; [1,2]DITHIOLO[1,4]THIAZINE DITHIONE;

ARTICLE; CATALYSIS; CYCLIC POTENTIOMETRY; CYCLOADDITION; DRUG SYNTHESIS; ISOMER; REACTION ANALYSIS;

EID: 2442662862     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035748p     Document Type: Article

References (37)

1. Sudakin, D. L. J. Toxicol.-Clin. Toxicol. 2003, 41, 195-204.
2. (a) Yao, K.-S.; O'Dwyer, P. J. Biochem. Pharmacol. 2003, 66, 15-23.
3. (b) Miao, W.; Hu, L.; Kandouz, M.; Batist, G. Mol. Pharmacol. 2003, 64, 346-354.
4. Kwak, M.-K.; Wakabayashi, N.; Itoh, K.; Motohashi, H.; Yamamoto, M.; Kensler, T. W. J. Biol. Chem. 2003, 278, 8135-8145.
5. Curphey, T. J. J. Org. Chem. 2002, 67, 6461-6473.
6. (a) Chatterji, T.; Kizil, M.; Keerthi, K.; Chowdhury, G.; Pospísil, T.; Gates, K. S. J. Am. Chem. Soc. 2003, 125, 4996-4997.
7. (b) Breydo, L.; Gates, K. S. J. Org. Chem. 2002, 67, 9054-9060.
8. Kanda, Y.; Ashizawa, T.; Kawashima, K.; Ikeda, S.; Tamaoki, T. Bioorg. Med. Chem. Lett. 2003, 13, 455-458.
9. (b) Lee, A. H. F.; Chan, A. S. C.; Li, T. Tetrahedron 2003, 59, 833-839.
10. (a) Marcos, C. F.; Polo, C.; Rakitin, O. A.; Rees, C. W.; Torroba, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 281-283.
11. (b) Rees, C. W.; White, A. J. P.; Williams, D. J.; Rakitin, O. A.; Marcos, C. F.; Polo, C.; Torroba, T. J. Org. Chem. 1998, 63, 2189-2196.
12. (c) Marcos, C. F.; Rakitin, O. A.; Rees, C. W.; Torroba, T.; White, A. J. P.; Williams, D. J. Chem. Commun. 1999, 29-30.
13. (a) Marcos, C. F.; Polo, C.; Rakitin, O. A.; Rees, C. W.; Torroba, T. J. Chem. Soc., Chem. Commun. 1997, 879-880.
14. (b) Konstantinova, L. S.; Obruchnikova, N. V.; Rakitin, O. A.; Rees, C. W.; Torroba, T. J. Chem. Soc., Perkin Trans. 1 2000, 3421-3427.
15. (a) Marcos, C. F.; Rakitin, O. A.; Rees, C. W.; Souvorova, L. I.; Torroba, T.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1998, 453-454.
16. (b) Rees, C. W.; White, A. J. P.; Williams, D. J.; Rakitin, O. A.; Marcos, C. F.; Torroba, T. J. Org. Chem. 1999, 64, 5010-5016.
17. (a) Barriga, S.; Konstantinova, L. S.; Marcos, C. F.; Rakitin, O. A.; Rees, C. W.; Torroba, T.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Perkin Trans. 1 1999, 2237-2241.
18. (b) García-Valverde, M.; Pascual, R.; Torroba, T. Org. Lett. 2003, 5, 929-932.
19. Rees, C. W.; Rakitin, O. A.; Marcos, C. F.; Torroba, T. J. Org. Chem. 1999, 64, 4376-4380.
20. (a) Barriga, S.; Fuertes, P.; Marcos, C. F.; Miguel, D.; Rakitin, O. A.; Rees, C. W.; Torroba, T. J. Org. Chem. 2001, 66, 5766-5771.
21. (b) Barriga, S.; Fuertes, P.; Marcos, C. F.; Rakitin, O. A.; Torroba, T. J. Org. Chem. 2002, 67, 6439-6448.
22. (c) Barriga, S.; Marcos, C. F.; Riant, O.; Torroba, T. Tetrahedron 2002, 58, 9785-9792.
23. Qi, J.; Li, T.; Chan, A. S. C. Bioorg. Med. Chem. Lett. 2003, 13, 3561-3563.
24. For reviews, see: (a) Pedersen, C. Th. Adv. Heterocycl. Chem. 1982, 31, 63-113; Sulfur Rep. 1995, 16, 173-213.
25. For reviews, see: (a) Pedersen, C. Th. Adv. Heterocycl. Chem. 1982, 31, 63-113; Sulfur Rep. 1995, 16, 173-213.
26. (b) McKinnon, D. M. In Comprehensive Heterocyclic Chemistry; Katrizky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 6, Chapter 4.31, pp 783-811. Comprehensive Heterocyclic Chemistry II; Katrizky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Sci.: Oxford, 1996; Vol. 3, Chapter 3.11, pp 569-605.
27. (b) McKinnon, D. M. In Comprehensive Heterocyclic Chemistry; Katrizky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 6, Chapter 4.31, pp 783-811. Comprehensive Heterocyclic Chemistry II; Katrizky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Sci.: Oxford, 1996; Vol. 3, Chapter 3.11, pp 569-605.
28. (a) Doxsee, D. D.; Gallaway, C. P.; Rauchfuss, T. B.; Wilson, S. R.; Yang, X. Inorg. Chem. 1993, 32, 5467-5471.
29. (b) Fanghänel, E.; Palmer, T.; Kersten, J.; Ludwigs, R.; von Schnering, H. G. Synthesis 1994, 1067-1071.
30. (a) Lutz, R. E.; Smithey, W. R., Jr. J. Org. Chem. 1951, 16, 51-56.
31. (b) Lutz, R. E. J. Am. Chem. Soc. 1926, 48, 2905-2915.
32. (a) Blomquist, A. T.; Winslow, E. C. J. Org. Chem. 1945, 10, 149-158.
33. (b) Hopf, H.; Witulski, B. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; Chapter 2, pp 60-61.
34. Barriga, S.; García, N.; Marcos, C. F.; Neo, A. G.; Torroba, T. Arkivoc 2002, vi, 212-223.
35. Skabara, P. J.; Serebryakov, I. M.; Roberts, D. M.; Perepichka, I. F.; Coles, S. J.; Hursthouse, M. B. J. Org. Chem. 1999, 64, 6418-6424.
36. Friebolin, H. Basic One- and Two-Dimensional NMR Spectroscopy, 3rd ed.; Wiley-VCH: Weinheim, 1998; Chapter 11.
37. HyperChem 5.11 (Hypercube, Inc.).