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Volumn , Issue 5, 2005, Pages 809-812

A new preparative route to substituted carbazoles by benzannulation

Author keywords

Annulations; Carbazoles; Enynes; Heterocycles; Phenols

Indexed keywords

ACETIC ACID; ACETIC ANHYDRIDE; AMINE; ANILINE DERIVATIVE; CARBAZOLE DERIVATIVE; CARBONYL DERIVATIVE; IODINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFUR DERIVATIVE; TOLUENE DERIVATIVE;

EID: 15944419206     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-863741     Document Type: Article
Times cited : (15)

References (41)
  • 2
    • 77957036993 scopus 로고
    • Brossi, A., Ed.; Academic Press: New York
    • (b) Chakraborty, D. P. In The Alkaloids, Vol. 44; Brossi, A., Ed.; Academic Press: New York, 1993, 257.
    • (1993) The Alkaloids , vol.44 , pp. 257
    • Chakraborty, D.P.1
  • 8
    • 0001426611 scopus 로고    scopus 로고
    • Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Elsevier: Oxford
    • Sunderg, R. J. In Comprehensive Heterocyclic Chemistry II, Vol. 2; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Elsevier: Oxford, 1996, 119.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.2 , pp. 119
    • Sunderg, R.J.1
  • 31
    • 15944414407 scopus 로고    scopus 로고
    • note
    • (a) 2-Iodoaniline 8a is commercially available. The substituted 2-iodoanilines 8b, 8c and 8e were prepared from the commercially available 4-methylaniline, 2-nitro-4-methoxyaniline and 4-fluoroaniline, respectively, according to the procedure described by Ma et al.12b Ethyl 4-amino-3- iodobenzoate 8d and 4-nitro-2-iodoaniline 8f were prepared from commercially available ethyl 4-aminobenzoate and 4-nitroaniline, respectively by iodination according to the procedure described by Spivey et al. and Adimurthy et al., respectively.12c,d
  • 36
    • 15944420394 scopus 로고    scopus 로고
    • note
    • 3N as base and an equimolar amount of copper and palladium catalysts (0.01 equiv). Iododerivatives 9d and 9f show low solubility in THF and a mixture of THF-DMF was used as solvent.
  • 37
    • 15944376744 scopus 로고    scopus 로고
    • note
    • 3 was adjusted depending on the solubility of the starting aldehydes. The above-mentioned reaction proceeds slowly at r.t. (typically 2 d). Notably, worse results have been obtained by heating the reaction mixture.
  • 39
    • 0000035972 scopus 로고
    • (a) Only E-isomers of acids 13 were obtained (NMR analysis). The Wittig reaction of ylide 12 with the aldehydes affords the 3-(E)-alkylidene-succinic acid monoalkyl esters in a highly stereoselective way; for previous studies on this reaction see: Paquette, L. A.; Schulze, M. M.; Bolin, D. J. Org. Chem. 1994, 59, 2043.
    • (1994) J. Org. Chem. , vol.59 , pp. 2043
    • Paquette, L.A.1    Schulze, M.M.2    Bolin, D.3
  • 41
    • 15944412340 scopus 로고    scopus 로고
    • note
    • +], 427, 382, 354, 334, 315, 290, 272, 244, 227, 200, 171, 155, 139, 120, 91, 65.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.