Nucleophilic addition reactions of 2-nitro-1-(phenylsulfonyl)indole. A new synthesis of 3-substituted-2-nitroindoles

Tetrahedron Letters

Volumn 40, Issue 43, 1999, Pages 7615-7619

  Pelkey, Erin T ^a   Barden, Timothy C ^a   Gribble, Gordon W ^a  

^a Lamont Doherty Earth Observatory   (United States)

Author keywords

1,3 Dipolar cycloaddition; 2 Nitroindoles; Isoxazolo 5,4 b indole; Nucleophilic addition

Indexed keywords

COPPER DERIVATIVE; CYCLOHEXANONE; INDOLE; INDOLE DERIVATIVE; MALONIC ACID DERIVATIVE; NITRO DERIVATIVE; TETRANITROMETHANE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; ISOMERISM; REACTION ANALYSIS; SYNTHESIS;

EID: 0033595861     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01557-9     Document Type: Article

References (27)

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6. For an excellent review of nucleophilic addition reactions to indoles, see: Joule, J. A. Prog. Het. Chem. 1999, 11, 45-65.
7. 6: C, 56.25; H, 5.03; N, 8.75. Found: C, 56.28; H, 5.20; N, 8.64.
8. 3: C, 65.11; H, 5.46; N, 10.85. Found: C, 64.86; H, 5.46; N, 10.60.
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10. +) 277.0851, found 277.0855.
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14. 3N: C, 62.97; H, 3.96; N, 3.67; S, 16.81. Found: C, 63.06; H, 3.98; N, 3.66; S, 16.80.
15. 2N: C, 66.40; H, 4.83; N, 5.16; S, 11.82. Found: C, 66.40; H, 4.86; N, 5.16; S, 11.78. This reaction also produced a small quantity of 3-methyl-1- (phenylsulfonyl)indole, by comparison with an authentic sample.
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20. 4/DMSO affords the corresponding 1-nitro olefins: Corey, E. J.; Estreicher, H. Tetrahedron Lett. 1980, 21, 1113-1116; this method has been used for the synthesis of 2-nitrobenzofurans: Einhorn, J.; Demerseman, P.; Royer, R. Synthesis 1984, 978-980.
21. 4/DMSO affords the corresponding 1-nitro olefins: Corey, E. J.; Estreicher, H. Tetrahedron Lett. 1980, 21, 1113-1116; this method has been used for the synthesis of 2-nitrobenzofurans: Einhorn, J.; Demerseman, P.; Royer, R. Synthesis 1984, 978-980.
22. 5S: C, 52.48; H, 2.64; N, 12.24; S, 9.34. Found: C, 52.73; H, 2.64; N, 12.07; S, 9.30.
23. 2Ph-MeOH: 100%), 130, 102, 77.
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26. 1
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