Cyclic amination onto aromatic ring of sulfonamides with (diacetoxyiodo)arenes: Effect of sulfonyl group

Tetrahedron Letters

Volumn 37, Issue 34, 1996, Pages 6129-6132

  Togo, Hideo ^a   Hoshina, Yoichiro ^a   Yokoyama, Masataka ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

(DIACETOXYIODO)ARENE; 1,2,3,4 TETRAHYDROQUINOLINE DERIVATIVE; AMINE; IODINE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFONAMIDE; TUNGSTEN; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; IRRADIATION;

EID: 0030593606     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01292-0     Document Type: Article

References (34)

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3. 1. Magnus, P.; Parry, D.; Iliadis, T.; Eisenbeis, S. A.; Fairhurst, R. A. J. Chem. Soc., Chem. Commun. 1994, 1543-1544; Morimoto, Y.; Matsuda, F.; Shirahama, H. Synlett 1991, 202-203; Daruwala, A. B.; Gearien, J. E.; Dunn III, W. J.; Benoit, P. S.; Bauer, L. J. Med. Chem. 1974, 17, 819-824; Staub, G. M.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. J. Am. Chem. Soc. 1992, 114, 1015-1017; Neville, C. F.; Grundon, M. F.; Ramachandran, V. N.; Reisch, J. J. Chem. Soc., Perkin 1 1991, 259-262; Gellerman, G.; Babad, M.; Kashman, Y. Tetrahedron Lett. 1993, 34, 1827-1830.
4. 1. Magnus, P.; Parry, D.; Iliadis, T.; Eisenbeis, S. A.; Fairhurst, R. A. J. Chem. Soc., Chem. Commun. 1994, 1543-1544; Morimoto, Y.; Matsuda, F.; Shirahama, H. Synlett 1991, 202-203; Daruwala, A. B.; Gearien, J. E.; Dunn III, W. J.; Benoit, P. S.; Bauer, L. J. Med. Chem. 1974, 17, 819-824; Staub, G. M.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. J. Am. Chem. Soc. 1992, 114, 1015-1017; Neville, C. F.; Grundon, M. F.; Ramachandran, V. N.; Reisch, J. J. Chem. Soc., Perkin 1 1991, 259-262; Gellerman, G.; Babad, M.; Kashman, Y. Tetrahedron Lett. 1993, 34, 1827-1830.
5. 1. Magnus, P.; Parry, D.; Iliadis, T.; Eisenbeis, S. A.; Fairhurst, R. A. J. Chem. Soc., Chem. Commun. 1994, 1543-1544; Morimoto, Y.; Matsuda, F.; Shirahama, H. Synlett 1991, 202-203; Daruwala, A. B.; Gearien, J. E.; Dunn III, W. J.; Benoit, P. S.; Bauer, L. J. Med. Chem. 1974, 17, 819-824; Staub, G. M.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. J. Am. Chem. Soc. 1992, 114, 1015-1017; Neville, C. F.; Grundon, M. F.; Ramachandran, V. N.; Reisch, J. J. Chem. Soc., Perkin 1 1991, 259-262; Gellerman, G.; Babad, M.; Kashman, Y. Tetrahedron Lett. 1993, 34, 1827-1830.
6. 1. Magnus, P.; Parry, D.; Iliadis, T.; Eisenbeis, S. A.; Fairhurst, R. A. J. Chem. Soc., Chem. Commun. 1994, 1543-1544; Morimoto, Y.; Matsuda, F.; Shirahama, H. Synlett 1991, 202-203; Daruwala, A. B.; Gearien, J. E.; Dunn III, W. J.; Benoit, P. S.; Bauer, L. J. Med. Chem. 1974, 17, 819-824; Staub, G. M.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. J. Am. Chem. Soc. 1992, 114, 1015-1017; Neville, C. F.; Grundon, M. F.; Ramachandran, V. N.; Reisch, J. J. Chem. Soc., Perkin 1 1991, 259-262; Gellerman, G.; Babad, M.; Kashman, Y. Tetrahedron Lett. 1993, 34, 1827-1830.
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9. 3. Neumann, W. P. Synthesis 1987, 665-683; Curran, D. P. Synthesis 1988, 417-439, 489-513: Smadja, W. Synlett 1994, 1-26; Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, ed. Baldwin, J. E. Pergamon Press, Oxford, 1986.
10. 3. Neumann, W. P. Synthesis 1987, 665-683; Curran, D. P. Synthesis 1988, 417-439, 489-513: Smadja, W. Synlett 1994, 1-26; Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, ed. Baldwin, J. E. Pergamon Press, Oxford, 1986.
11. 3. Neumann, W. P. Synthesis 1987, 665-683; Curran, D. P. Synthesis 1988, 417-439, 489-513: Smadja, W. Synlett 1994, 1-26; Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, ed. Baldwin, J. E. Pergamon Press, Oxford, 1986.
12. 4. Amination onto aromatic ring via aminyl radical: Minisci, F.; Galli, R. Tetrahedron Lett. 1966, 2531-2533; Glover, S. A.; Goosen, A.; Laue, H. A. H. J. Chem. Soc., Perkin 1 1973, 1647-1650; Amination onto aromatic ring via iminyl radical: Forrester, A. R.; Gill, M.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1976, 677-678; Forrester, A. R.; Gill, M.; Sadd, J. S.; Thomson, R. H. ibid. 1975, 291-292; Hofmann-Löffler reaction: Corey E. J.; Hertler, W. R. J. Am. Chem. Soc. 1960, 82, 1657-1608; Hertler, W. R.; Corey, E. J. J. Org. Chem. 1959, 24, 572-573; Buchschacher, P.; Kalvoda, J.; Arigoni, D.; Jeger, O. J. Am. Chem. Soc. 1958, 80, 2905-2906.
13. 4. Amination onto aromatic ring via aminyl radical: Minisci, F.; Galli, R. Tetrahedron Lett. 1966, 2531-2533; Glover, S. A.; Goosen, A.; Laue, H. A. H. J. Chem. Soc., Perkin 1 1973, 1647-1650; Amination onto aromatic ring via iminyl radical: Forrester, A. R.; Gill, M.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1976, 677-678; Forrester, A. R.; Gill, M.; Sadd, J. S.; Thomson, R. H. ibid. 1975, 291-292; Hofmann-Löffler reaction: Corey E. J.; Hertler, W. R. J. Am. Chem. Soc. 1960, 82, 1657-1608; Hertler, W. R.; Corey, E. J. J. Org. Chem. 1959, 24, 572-573; Buchschacher, P.; Kalvoda, J.; Arigoni, D.; Jeger, O. J. Am. Chem. Soc. 1958, 80, 2905-2906.
14. 4. Amination onto aromatic ring via aminyl radical: Minisci, F.; Galli, R. Tetrahedron Lett. 1966, 2531-2533; Glover, S. A.; Goosen, A.; Laue, H. A. H. J. Chem. Soc., Perkin 1 1973, 1647-1650; Amination onto aromatic ring via iminyl radical: Forrester, A. R.; Gill, M.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1976, 677-678; Forrester, A. R.; Gill, M.; Sadd, J. S.; Thomson, R. H. ibid. 1975, 291-292; Hofmann-Löffler reaction: Corey E. J.; Hertler, W. R. J. Am. Chem. Soc. 1960, 82, 1657-1608; Hertler, W. R.; Corey, E. J. J. Org. Chem. 1959, 24, 572-573; Buchschacher, P.; Kalvoda, J.; Arigoni, D.; Jeger, O. J. Am. Chem. Soc. 1958, 80, 2905-2906.
15. 4. Amination onto aromatic ring via aminyl radical: Minisci, F.; Galli, R. Tetrahedron Lett. 1966, 2531-2533; Glover, S. A.; Goosen, A.; Laue, H. A. H. J. Chem. Soc., Perkin 1 1973, 1647-1650; Amination onto aromatic ring via iminyl radical: Forrester, A. R.; Gill, M.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1976, 677-678; Forrester, A. R.; Gill, M.; Sadd, J. S.; Thomson, R. H. ibid. 1975, 291-292; Hofmann-Löffler reaction: Corey E. J.; Hertler, W. R. J. Am. Chem. Soc. 1960, 82, 1657-1608; Hertler, W. R.; Corey, E. J. J. Org. Chem. 1959, 24, 572-573; Buchschacher, P.; Kalvoda, J.; Arigoni, D.; Jeger, O. J. Am. Chem. Soc. 1958, 80, 2905-2906.
16. 4. Amination onto aromatic ring via aminyl radical: Minisci, F.; Galli, R. Tetrahedron Lett. 1966, 2531-2533; Glover, S. A.; Goosen, A.; Laue, H. A. H. J. Chem. Soc., Perkin 1 1973, 1647-1650; Amination onto aromatic ring via iminyl radical: Forrester, A. R.; Gill, M.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1976, 677-678; Forrester, A. R.; Gill, M.; Sadd, J. S.; Thomson, R. H. ibid. 1975, 291-292; Hofmann-Löffler reaction: Corey E. J.; Hertler, W. R. J. Am. Chem. Soc. 1960, 82, 1657-1608; Hertler, W. R.; Corey, E. J. J. Org. Chem. 1959, 24, 572-573; Buchschacher, P.; Kalvoda, J.; Arigoni, D.; Jeger, O. J. Am. Chem. Soc. 1958, 80, 2905-2906.
17. 4. Amination onto aromatic ring via aminyl radical: Minisci, F.; Galli, R. Tetrahedron Lett. 1966, 2531-2533; Glover, S. A.; Goosen, A.; Laue, H. A. H. J. Chem. Soc., Perkin 1 1973, 1647-1650; Amination onto aromatic ring via iminyl radical: Forrester, A. R.; Gill, M.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1976, 677-678; Forrester, A. R.; Gill, M.; Sadd, J. S.; Thomson, R. H. ibid. 1975, 291-292; Hofmann-Löffler reaction: Corey E. J.; Hertler, W. R. J. Am. Chem. Soc. 1960, 82, 1657-1608; Hertler, W. R.; Corey, E. J. J. Org. Chem. 1959, 24, 572-573; Buchschacher, P.; Kalvoda, J.; Arigoni, D.; Jeger, O. J. Am. Chem. Soc. 1958, 80, 2905-2906.
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26. 7. General procedure is as follows: To a solution of sulfonamide (0.5 mmol) in 1,2-dichloroethane (7 ml) were added (diacetoxyiodo)benzene (0.8 mmol) and iodine (0.5 mmol). The mixture was irradiated at 60-65°C with a tungsten lamp (500 W) for 2 h under argon atmosphere. After the reaction, the mixture was poured into chloroform and washed with aq. sodium sulfite solution and subsequently with water. The organic layer was dried over sodium sulfate. After removal of the solvent, the residue was chromatographed on silica gel by pTLC to give the product.
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