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Volumn , Issue 11, 2003, Pages 1671-1678

Synthesis of 2-aryl-1-hydroxyazaindoles and 2-arylazaindoles via oxidation of o-hydroxyaminostyrylpyridines

Author keywords

1N hydroxy azaindoles; 2,3 dichloro 5,6 dicyano 1,4 benzoquinone (DDQ); Azaindoles; Cyclization; Oxidation; Pyrrolopyridines

Indexed keywords

ALDEHYDES; CONDENSATION; NITROGEN COMPOUNDS; OXIDATION; REDUCTION; SUBSTITUTION REACTIONS;

EID: 0041737779     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40884     Document Type: Article
Times cited : (27)

References (33)
  • 6
    • 84943376213 scopus 로고
    • Katritzky, A. R.; Rees, C. W.; Bird, C. W.; Cheeseman, G. W. H., Eds.; Pergamon: Oxford
    • (d) Greenhill, J. V. In Comprehensive Heterocyclic Chemistry Vol. 4; Katritzky, A. R.; Rees, C. W.; Bird, C. W.; Cheeseman, G. W. H., Eds.; Pergamon: Oxford, 1984, 497.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.4 , pp. 497
    • Greenhill, J.V.1
  • 12
    • 84932111134 scopus 로고
    • For a synthesis of 3-bromo-5-nitro-4-methylpyridine, see: Prokopov, A. A.; Yakhontov, L. N. Khim. Geterotsikl. Soedin. 1979, 15, 86; Chem. Heterocycl. Compd. (Engl. Transl.) 1979, 15: 76.
    • (1979) Khim. Geterotsikl. Soedin. , vol.15 , pp. 86
    • Prokopov, A.A.1    Yakhontov, L.N.2
  • 13
    • 0041445452 scopus 로고
    • For a synthesis of 3-bromo-5-nitro-4-methylpyridine, see: Prokopov, A. A.; Yakhontov, L. N. Khim. Geterotsikl. Soedin. 1979, 15, 86; Chem. Heterocycl. Compd. (Engl. Transl.) 1979, 15: 76.
    • (1979) Chem. Heterocycl. Compd. (Engl. Transl.) , vol.15 , pp. 76
  • 14
    • 0042447659 scopus 로고
    • For condensation conditions, see Ref. 4 and: (a) Herz, W.; Murty, D. R. K. J. Org. Chem. 1961, 26, 418. (b) Barraclough, P.; Beams, R. M.; Black, J. W. ; Cambridge, D.; Collard, D.; Demaine, D. A.; Firmin, D.; Gerskowitch, V. P.; Glen, R. C.; Giles, H.; Hill, A. P.; Hull, R. A. D.; Iyer, R.; King, W. R.; Livingstone, D. J.; Nobbs, M. S.; Randall, P.; Shah, G.; Vine, S. J.; Whiting, M. V. Eur. J. Med. Chem. 1990, 25, 467; Chem. Abstr. 1991, 114, 17097.
    • (1961) J. Org. Chem. , vol.26 , pp. 418
    • Herz, W.1    Murty, D.R.K.2
  • 16
    • 0042948572 scopus 로고
    • For condensation conditions, see Ref. 4 and: (a) Herz, W.; Murty, D. R. K. J. Org. Chem. 1961, 26, 418. (b) Barraclough, P.; Beams, R. M.; Black, J. W. ; Cambridge, D.; Collard, D.; Demaine, D. A.; Firmin, D.; Gerskowitch, V. P.; Glen, R. C.; Giles, H.; Hill, A. P.; Hull, R. A. D.; Iyer, R.; King, W. R.; Livingstone, D. J.; Nobbs, M. S.; Randall, P.; Shah, G.; Vine, S. J.; Whiting, M. V. Eur. J. Med. Chem. 1990, 25, 467; Chem. Abstr. 1991, 114, 17097.
    • (1991) Chem Abstr. , vol.114 , pp. 17097
  • 22
    • 0041946944 scopus 로고    scopus 로고
    • note
    • 3 rather than 1 N aq NaOH as described by the authors
  • 27
    • 0041946945 scopus 로고    scopus 로고
    • note
    • (b) Alternatively, 2-methyl-3-nitropyridine was prepared from 2-chloro-3-nitropyridine in 66% yield via displacement of the chloride with the sodium salt of diethyl malonate in DMF at 0°C followed by hydrolysis and decarboxylation in 6 N aq HCl for 4 h at reflux
  • 32
    • 0041946943 scopus 로고    scopus 로고
    • note
    • (a) Compound 19 was prepared from 3-hydroxy-2-nitropyridine via formation of the triflate followed by a Suzuki coupling with trans-4-vinylphenylboronic acid


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.