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Volumn 74, Issue 24, 2009, Pages 9440-9445

Synthesis of functionalized pyridazin-3(2H)-ones via bromine-magnesium exchange on bromopyridazin-3(2H)-ones

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION-ELIMINATION; BROMINE-MAGNESIUM EXCHANGE; CHEMICAL EQUATIONS; ELECTROPHILES; EXCHANGE REACTION; FUNCTIONALIZATIONS; FUNCTIONALIZED; METALATIONS; METHOXY; MODEL SUBSTRATES; NUCLEOPHILIC SUBSTITUTIONS; TANDEM REACTION;

EID: 73149102320     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9020985     Document Type: Article
Times cited : (14)

References (40)
  • 1
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    • For reviews dealing with the synthesis, functionalization and applications of pyridazines and pyridazin-3(2H)-ones see: (a) Kolar, P.; Tišler, M. Adv. Heterocycl. Chem. 1999, 75, 167.
    • For reviews dealing with the synthesis, functionalization and applications of pyridazines and pyridazin-3(2H)-ones see: (a) Kolar, P.; Tišler, M. Adv. Heterocycl. Chem. 1999, 75, 167.
  • 2
    • 84862371000 scopus 로고    scopus 로고
    • Attanasi, O. A, Spinelli, D, Eds, Societa Chimica Italiana: Rome
    • (b) Tapolcsányi, P.; Mátyus, P. In Targets in Heterocyclic Systems; Attanasi, O. A., Spinelli, D., Eds.; Societa Chimica Italiana: Rome, 2002, Vol. 6, p 369.
    • (2002) Targets in Heterocyclic Systems , vol.6 , pp. 369
    • Tapolcsányi, P.1    Mátyus, P.2
  • 3
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    • Yamamoto, Y, Ed, Thieme: New York
    • (c) Haider, N., Holzer, W. In Science of Synthesis; Yamamoto, Y., Ed.; Thieme: New York, 2004, Vol. 16, p 125.
    • (2004) Science of Synthesis , vol.16 , pp. 125
    • Haider, N.1    Holzer, W.2
  • 4
    • 84906437365 scopus 로고    scopus 로고
    • Katritzky, A. R, Ramsden, C. A, Scriven, E. F. V, Taylor, R. J. K, Aitken, A, Eds; Elsevier: New York
    • (d) Maes, B. U. W., Lemière, G. L. F. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R., Ramsden, C. A., Scriven, E. F. V., Taylor, R. J. K., Aitken, A., Eds; Elsevier: New York, 2008, Vol. 8, p 1.
    • (2008) Comprehensive Heterocyclic Chemistry III , vol.8 , pp. 1
    • Maes, B.U.W.1    Lemière, G.L.F.2
  • 7
    • 85196232388 scopus 로고    scopus 로고
    • For reviews dealing with Pd-catalyzed reactions on halopyridazines and halopyridazin-3(2H)-ones see: (a) Maes, B. U. W.; Tapolcsányi, P.; Meyers, C.; Mátyus, P. Curr. Org. Chem. 2006, 10, 377.
    • For reviews dealing with Pd-catalyzed reactions on halopyridazines and halopyridazin-3(2H)-ones see: (a) Maes, B. U. W.; Tapolcsányi, P.; Meyers, C.; Mátyus, P. Curr. Org. Chem. 2006, 10, 377.
  • 8
    • 73149107325 scopus 로고    scopus 로고
    • Maes, B. U. W. In Palladium in Heterocyclic Chemistry; Tetrahedron Organic Chemistry Series; Li, J. J., Gribble, G. W., Eds.; Elsevier: New York, 2006, 26, p 541.
    • (b) Maes, B. U. W. In Palladium in Heterocyclic Chemistry; Tetrahedron Organic Chemistry Series; Li, J. J., Gribble, G. W., Eds.; Elsevier: New York, 2006, Vol. 26, p 541.
  • 9
    • 73149085580 scopus 로고    scopus 로고
    • For selected examples of Pd-catalyzed reactions on halopyridazines and halopyridazin-3(2H)-ones see: (a) Turck, A.; Plé, N.; Mojovic, L.; Quéguiner, G. Bull. Soc. Chim. Fr. 1993, 130, 488.
    • For selected examples of Pd-catalyzed reactions on halopyridazines and halopyridazin-3(2H)-ones see: (a) Turck, A.; Plé, N.; Mojovic, L.; Quéguiner, G. Bull. Soc. Chim. Fr. 1993, 130, 488.
  • 33
    • 73149105565 scopus 로고    scopus 로고
    • The scope of the process is unfortunately usually limited to electron rich pyridazines avoiding competitive addition reactions. For the addition reaction of s-BuLi on pyridazines and pyridazin-3(2H)-ones see Dal Piaz, V, Capperucci, A. Synlett 1998, 762
    • The scope of the process is unfortunately usually limited to electron rich pyridazines avoiding competitive addition reactions. For the addition reaction of s-BuLi on pyridazines and pyridazin-3(2H)-ones see Dal Piaz, V.; Capperucci, A. Synlett 1998, 762.
  • 37
    • 73149092391 scopus 로고    scopus 로고
    • A similar reaction involving the additional substitution of a C-4 halogen by a dimethylamino group was observed when using 3,6-dimethoxy-4,5-diodo- and 3,6-dimethoxy-4,5-dibromopyridazine as substrates, i-PrMgCl as halogen-magnesium exchange reagent and DMF as the electrophile: see ref 5f
    • A similar reaction involving the additional substitution of a C-4 halogen by a dimethylamino group was observed when using 3,6-dimethoxy-4,5-diodo- and 3,6-dimethoxy-4,5-dibromopyridazine as substrates, i-PrMgCl as halogen-magnesium exchange reagent and DMF as the electrophile: see ref 5f.
  • 38
    • 0036262798 scopus 로고    scopus 로고
    • For ipso substitutions in (η6-arene)tricarbonylchromium, see
    • 6-arene)tricarbonylchromium, see: Rose-Munch, F.; Rose, E. Eur. J. Inorg. Chem. 2002, 6, 1269.
    • (2002) Eur. J. Inorg. Chem , vol.6 , pp. 1269
    • Rose-Munch, F.1    Rose, E.2
  • 39
    • 73149087114 scopus 로고    scopus 로고
    • For regioselective bromine-magnesium exchange in dibromopyridines, see: Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron 2000, 56, 1349. For regioselective bromine-magnesium exchange in 4,5-dibromo-2,6-dimethoxypyrimidine see: Boudet, N.; Knochel, P. Org. Lett. 2006, 8, 3737.
    • For regioselective bromine-magnesium exchange in dibromopyridines, see: Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron 2000, 56, 1349. For regioselective bromine-magnesium exchange in 4,5-dibromo-2,6-dimethoxypyrimidine see: Boudet, N.; Knochel, P. Org. Lett. 2006, 8, 3737.
  • 40
    • 73149116976 scopus 로고    scopus 로고
    • A Scifinder database search revealed that 70% of the molecules synthesized in this manuscript (with the specific substituents on C-4 and C-5 shown in the tables, schemes and figures, leaving the N-2 and C-6 substituents undefined) were hitherto unknown.
    • A Scifinder database search revealed that 70% of the molecules synthesized in this manuscript (with the specific substituents on C-4 and C-5 shown in the tables, schemes and figures, leaving the N-2 and C-6 substituents undefined) were hitherto unknown.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.