Reactions of 3H-1,2-benzodithiol-3-one 1-oxide with amines and anilines

Tetrahedron Letters

Volumn 37, Issue 30, 1996, Pages 5337-5340

  Kim, Woongki ^a   Dannaldson, Jeffrey ^a   Gates, Kent S ^a,b  

^a UNIVERSITY OF MISSOURI   (United States)

^b University of Missouri   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 BENZISOTHIAZOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030598064     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01124-0     Document Type: Article

References (32)

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7. 5. We find that 1 reacts with nucleic acid model, 9-ethyl adenine in dichloromethane. The product(s) of this reaction are, as yet, uncharacterized.
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19. 5NOS: 151.0092, found 151.0091 (-0.3 ppm). Elemental sulfur is observed (by thin layer chromatography) as a product of these reactions. Sulfur was isolated and characterized from the reaction of 1 with phenethylamine. Anal. calcd for S: S 100%. Found: S 99.7 %.
20. 9. Fleury, M. B.; Largeron, M.; Barreu, M.; Vuilhorgne, M. Tetrahedron 1985, 41, 3705-3715. See also: Smutny, E. J.; Turner, W.; Morgan, E. D.; Robinson, R. Tetrahedron 1967, 23, 3785-3799.
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29. 14. Nogami, H.; Hasegawa, J.; Aoki, K. Chem. Pharm. Bull. 1971, 19, 2472-2477. Note: Under the reaction conditions reported here, 3H-1,2-benzodithiol-3-one (S-deoxy-1) shows little reactivity with the aniline nucleophiles examined in this study. S-deoxy-1 reacts relatively slowly with phenethylamine and cyclohexylamine, but does not afford the benzisothiazolinone products (2). It is reported that treatment of S-deoxy-1 with monosubstituted nitrogen nucleophiles or ammonia in alcoholic solution results in a reaction that yields 2,2′-dithiobis(benzamides) and 1,2-benzisothiazolin-3(2//)-one respectively: McKibben, M.; McClellend, E. W. J. Chem. Soc. 1923, 123, 170-173. McClelland, E. W.; Longwell, J. J. Chem. Soc. 1923, 123, 3310-3315. For related reactions of 3H-1,2-benzodithiole-3-thione with amines see: Pregnolato, M.; Borgna, P.; Terreni, M. J. Heterocyclic Chem. 1995, 32, 847-850.
30. 14. Nogami, H.; Hasegawa, J.; Aoki, K. Chem. Pharm. Bull. 1971, 19, 2472-2477. Note: Under the reaction conditions reported here, 3H-1,2-benzodithiol-3-one (S-deoxy-1) shows little reactivity with the aniline nucleophiles examined in this study. S-deoxy-1 reacts relatively slowly with phenethylamine and cyclohexylamine, but does not afford the benzisothiazolinone products (2). It is reported that treatment of S-deoxy-1 with monosubstituted nitrogen nucleophiles or ammonia in alcoholic solution results in a reaction that yields 2,2′-dithiobis(benzamides) and 1,2-benzisothiazolin-3(2//)-one respectively: McKibben, M.; McClellend, E. W. J. Chem. Soc. 1923, 123, 170-173. McClelland, E. W.; Longwell, J. J. Chem. Soc. 1923, 123, 3310-3315. For related reactions of 3H-1,2-benzodithiole-3-thione with amines see: Pregnolato, M.; Borgna, P.; Terreni, M. J. Heterocyclic Chem. 1995, 32, 847-850.
31. 14. Nogami, H.; Hasegawa, J.; Aoki, K. Chem. Pharm. Bull. 1971, 19, 2472-2477. Note: Under the reaction conditions reported here, 3H-1,2-benzodithiol-3-one (S-deoxy-1) shows little reactivity with the aniline nucleophiles examined in this study. S-deoxy-1 reacts relatively slowly with phenethylamine and cyclohexylamine, but does not afford the benzisothiazolinone products (2). It is reported that treatment of S-deoxy-1 with monosubstituted nitrogen nucleophiles or ammonia in alcoholic solution results in a reaction that yields 2,2′-dithiobis(benzamides) and 1,2-benzisothiazolin-3(2//)-one respectively: McKibben, M.; McClellend, E. W. J. Chem. Soc. 1923, 123, 170-173. McClelland, E. W.; Longwell, J. J. Chem. Soc. 1923, 123, 3310-3315. For related reactions of 3H-1,2-benzodithiole-3-thione with amines see: Pregnolato, M.; Borgna, P.; Terreni, M. J. Heterocyclic Chem. 1995, 32, 847-850.
32. 14. Nogami, H.; Hasegawa, J.; Aoki, K. Chem. Pharm. Bull. 1971, 19, 2472-2477. Note: Under the reaction conditions reported here, 3H-1,2-benzodithiol-3-one (S-deoxy-1) shows little reactivity with the aniline nucleophiles examined in this study. S-deoxy-1 reacts relatively slowly with phenethylamine and cyclohexylamine, but does not afford the benzisothiazolinone products (2). It is reported that treatment of S-deoxy-1 with monosubstituted nitrogen nucleophiles or ammonia in alcoholic solution results in a reaction that yields 2,2′-dithiobis(benzamides) and 1,2-benzisothiazolin-3(2//)-one respectively: McKibben, M.; McClellend, E. W. J. Chem. Soc. 1923, 123, 170-173. McClelland, E. W.; Longwell, J. J. Chem. Soc. 1923, 123, 3310-3315. For related reactions of 3H-1,2-benzodithiole-3-thione with amines see: Pregnolato, M.; Borgna, P.; Terreni, M. J. Heterocyclic Chem. 1995, 32, 847-850.