A New and Facile Method for the Synthesis of Nitrocarbazoles by Urea Nitrate

Synthetic Communications

Volumn 34, Issue 7, 2004, Pages 1259-1264

  Nagarajan, Rajagopal ^a   Muralidharan, D ^a   Perumal, Paramasivan T ^a  

^a CENTRAL LEATHER RESEARCH INSTITUTE   (India)

Author keywords

Acetylation; Carbazoles; Nitration; Nitrocarbazoles; Urea nitrate

Indexed keywords

ACETIC ACID; CARBAZOLE DERIVATIVE; NITRATE; NITROCARBAZOLE; UNCLASSIFIED DRUG; UREA DERIVATIVE; UREA NITRATE;

ACETYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; NITRATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 1842585972     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120030313     Document Type: Article

References (16)

1. (a) Knolker, H.-J.; Reddy, K.R. Isolation and synthesis of biologically active carbazole alkaloids. Chem. Rev. 2002, 102, 4303-4427;
2. 4-diene) iron complexes. Chem. Soc. Rev. 1999, 28, 151-157.
3. Buu-Hoi, Ng.Ph.; Royer, R. Potential nitrogen-heterocycle carcinogens. III. New derivatives of N-ethyl carbazole. J. Org. Chem. 1950, 15, 123-157.
4. (a) Babu, G.; Perumal, P.T. Synthetic applications of indium trichloride catalyzed reactions. Aldrichim. Acta 2000, 33, 16-22;
5. (b) Babu, G.; Perumal, P.T. Imino Diels-Alder reactions catalyzed by indium trichloride (InC13). Facile synthesis of quinoline and phenanthridinone derivatives. Tetrahedron Lett. 1997, 38, 5025-5026;
6. (c) Babu, G.; Nagarajan, R.; Natarajan, R.; Perumal, P.T. Indium trichloride-catalyzed imino Diels-Alder reactions: synthesis of new indolylquinoline derivatives. Synthesis 2000, 661-666.
7. Anniyappan, M.; Nagarajan, R.; Perumal, P.T. Urea nitrate catalyzed imino Diels-Alder reactions: synthesis of cyclopentaquinolines, pyranoquinolines and furoquinolines derivatives. Synth. Commun. 2002, 32, 99-103.
8. Anniyappan, M.; Muralidharan, D.; Perumal, P.T. A novel application of the oxidizing properties of urea nitrate and peroxydisulfate-cobalt(II): aromatization of NaD(P)H model Hantzsch 1,4-dihydropyridines. Tetrahedron 2002, 58, 5069-5073.
9. Storrie, F.R.; Tucker, S.H. Syntheses in the carbazole series. Alleged synthesis of 3-nitro-N-ethylcarbazole. J. Chem. Soc. 1931, 2255-2263.
10. Lindemann, R. Chemistry of carbazole. Ber. 1924, 57B, 555-559.
11. Morgan, G.T.; Mitchell, J.G. Search for trypanocidal activity. Derivatives of dehydrothio-p-toluidinesulfonic acid and of 3-aminocarbazoledisulfonic acid. J. Chem. Soc. 1931, 3279-3283.
12. Iles, D.H.; Ledwith, A. Charge transfer spectrums and reaction intermediates: photochemical nitration of carbazoles with tetranitromethane. J. Chem. Soc. D. Chem. Commun. 1969, 9, 364-365.
13. Ziersch, P. Carbazole derivatives. Ber. 1910, 42, 3977-3980.
14. Grotta, H.M.; Riggle, C.J.; Bearse, A.E. Dinitrocarbazoles. J. Org. Chem. 1964, 29, 2474-2476.
15. Kyziol, J.B.; Dasziewicz, Z.; Hetper, J. Fragmentation of some nitrocarbazoles and their 9-alkyl derivatives. Org. Mass Spectrom. 1987, 22 (1), 39-42.
16. Buu-Hoi, Hg.Ph.; Hoan, Ng. Potential nitrogen-heterocycle carcinogens. XII. 9-Ethyl carbazole-3-aldehyde and its derivatives. J. Org. Chem. 1951, 16, 1327-1332.