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Volumn 44, Issue 47, 2003, Pages 8545-8548

Novel analogues of 3-substituted-2,3-dihydro-1,4-dioxino[2,3-b]pyridines: Modifications in the dioxane ring

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DIHYDRO 1,4 DIOXINO[2,3 B]PYRIDINE; DIOXANE; METHYL GROUP; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0142169039     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.145     Document Type: Article
Times cited : (6)

References (28)
  • 1
    • 0033919896 scopus 로고    scopus 로고
    • For recent reports involving 2,3-dihydro-1,4-benzodioxin derivatives, see: (a) Czompa, A.; Dinya, Z.; Antus, S.; Varga, Z. Arch. Pharm. 2000, 333, 175-180; (b) Gu, W. X.; Jing, X. B.; Pan, X. F.; Chan, A. S. C.; Yang, T. K. Tetrahedron Lett. 2000, 41, 6079-6082; (c) Ward, R. S. Nat. Prod. Rep. 1999, 16, 75-96; (d) Bolognesi, M. L.; Budriesi, R.; Cavalli, A.; Chiarini, A.; Gotti, R.; Leonardi, A.; Minarini, A.; Poggesi, E.; Recanatini, M.; Rosini, M.; Tumiatti, V.; Melchiorre, C. J. Med. Chem. 1999, 42, 4214-4224; (d) Guillaumet, G. In Comprehensive Heterocyclic Chemistry II, 1st ed.; Katrizky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 6, pp. 447-463.
    • (2000) Arch. Pharm. , vol.333 , pp. 175-180
    • Czompa, A.1    Dinya, Z.2    Antus, S.3    Varga, Z.4
  • 2
    • 0034609172 scopus 로고    scopus 로고
    • For recent reports involving 2,3-dihydro-1,4-benzodioxin derivatives, see: (a) Czompa, A.; Dinya, Z.; Antus, S.; Varga, Z. Arch. Pharm. 2000, 333, 175-180; (b) Gu, W. X.; Jing, X. B.; Pan, X. F.; Chan, A. S. C.; Yang, T. K. Tetrahedron Lett. 2000, 41, 6079-6082; (c) Ward, R. S. Nat. Prod. Rep. 1999, 16, 75-96; (d) Bolognesi, M. L.; Budriesi, R.; Cavalli, A.; Chiarini, A.; Gotti, R.; Leonardi, A.; Minarini, A.; Poggesi, E.; Recanatini, M.; Rosini, M.; Tumiatti, V.; Melchiorre, C. J. Med. Chem. 1999, 42, 4214-4224; (d) Guillaumet, G. In Comprehensive Heterocyclic Chemistry II, 1st ed.; Katrizky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 6, pp. 447-463.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 6079-6082
    • Gu, W.X.1    Jing, X.B.2    Pan, X.F.3    Chan, A.S.C.4    Yang, T.K.5
  • 3
    • 0033083666 scopus 로고    scopus 로고
    • For recent reports involving 2,3-dihydro-1,4-benzodioxin derivatives, see: (a) Czompa, A.; Dinya, Z.; Antus, S.; Varga, Z. Arch. Pharm. 2000, 333, 175-180; (b) Gu, W. X.; Jing, X. B.; Pan, X. F.; Chan, A. S. C.; Yang, T. K. Tetrahedron Lett. 2000, 41, 6079-6082; (c) Ward, R. S. Nat. Prod. Rep. 1999, 16, 75-96; (d) Bolognesi, M. L.; Budriesi, R.; Cavalli, A.; Chiarini, A.; Gotti, R.; Leonardi, A.; Minarini, A.; Poggesi, E.; Recanatini, M.; Rosini, M.; Tumiatti, V.; Melchiorre, C. J. Med. Chem. 1999, 42, 4214-4224; (d) Guillaumet, G. In Comprehensive Heterocyclic Chemistry II, 1st ed.; Katrizky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 6, pp. 447-463.
    • (1999) Nat. Prod. Rep. , vol.16 , pp. 75-96
    • Ward, R.S.1
  • 4
    • 0033533802 scopus 로고    scopus 로고
    • For recent reports involving 2,3-dihydro-1,4-benzodioxin derivatives, see: (a) Czompa, A.; Dinya, Z.; Antus, S.; Varga, Z. Arch. Pharm. 2000, 333, 175-180; (b) Gu, W. X.; Jing, X. B.; Pan, X. F.; Chan, A. S. C.; Yang, T. K. Tetrahedron Lett. 2000, 41, 6079-6082; (c) Ward, R. S. Nat. Prod. Rep. 1999, 16, 75-96; (d) Bolognesi, M. L.; Budriesi, R.; Cavalli, A.; Chiarini, A.; Gotti, R.; Leonardi, A.; Minarini, A.; Poggesi, E.; Recanatini, M.; Rosini, M.; Tumiatti, V.; Melchiorre, C. J. Med. Chem. 1999, 42, 4214-4224; (d) Guillaumet, G. In Comprehensive Heterocyclic Chemistry II, 1st ed.; Katrizky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 6, pp. 447-463.
    • (1999) J. Med. Chem. , vol.42 , pp. 4214-4224
    • Bolognesi, M.L.1    Budriesi, R.2    Cavalli, A.3    Chiarini, A.4    Gotti, R.5    Leonardi, A.6    Minarini, A.7    Poggesi, E.8    Recanatini, M.9    Rosini, M.10    Tumiatti, V.11    Melchiorre, C.12
  • 5
    • 84944045237 scopus 로고    scopus 로고
    • Katrizky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: Oxford
    • For recent reports involving 2,3-dihydro-1,4-benzodioxin derivatives, see: (a) Czompa, A.; Dinya, Z.; Antus, S.; Varga, Z. Arch. Pharm. 2000, 333, 175-180; (b) Gu, W. X.; Jing, X. B.; Pan, X. F.; Chan, A. S. C.; Yang, T. K. Tetrahedron Lett. 2000, 41, 6079-6082; (c) Ward, R. S. Nat. Prod. Rep. 1999, 16, 75-96; (d) Bolognesi, M. L.; Budriesi, R.; Cavalli, A.; Chiarini, A.; Gotti, R.; Leonardi, A.; Minarini, A.; Poggesi, E.; Recanatini, M.; Rosini, M.; Tumiatti, V.; Melchiorre, C. J. Med. Chem. 1999, 42, 4214-4224; (d) Guillaumet, G. In Comprehensive Heterocyclic Chemistry II, 1st ed.; Katrizky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 6, pp. 447-463.
    • (1996) Comprehensive Heterocyclic Chemistry II, 1st Ed. , vol.6 , pp. 447-463
    • Guillaumet, G.1
  • 14
    • 85030972042 scopus 로고    scopus 로고
    • note
    • When the reaction was tried using NaH in DMF at room temperature or sodium methoxide in MeOH both, at room temperature and under reflux only starting material was recovered unaltered.
  • 15
    • 85030972349 scopus 로고    scopus 로고
    • note
    • 2/MeOH (25/1).
  • 16
    • 85030972246 scopus 로고    scopus 로고
    • note
    • Longer reaction times afforded mainly decomposition.
  • 17
    • 85030966824 scopus 로고    scopus 로고
    • note
    • +: 154.
  • 20
    • 85030968224 scopus 로고    scopus 로고
    • note
    • 2/acetone (9/1 and 4/1).
  • 21
    • 85030959852 scopus 로고    scopus 로고
    • note
    • +: 166.
  • 23
    • 85030972416 scopus 로고    scopus 로고
    • note
    • 2/acetone (9/1), to remove Lawesson's reagent by-products obtained in the course of the reaction and the second one, eluted with hexane/acetone (9/1), to obtain the pure compound.
  • 25
    • 85030954122 scopus 로고    scopus 로고
    • note
    • +: 184.
  • 27
    • 85030962699 scopus 로고    scopus 로고
    • 3 or NaH, no reaction took place.
    • 3 or NaH, no reaction took place.
  • 28
    • 85030968108 scopus 로고    scopus 로고
    • note
    • +: 181.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.