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Volumn 45, Issue 38, 2004, Pages 7157-7161

General facile synthesis of 2,5-diarylheteropentalenes

Author keywords

2,5 Diarylheteropentalenes; Bromination; Catalysis; Heterocycles; Suzuki

Indexed keywords

FURAN DERIVATIVE; HETEROCYCLIC COMPOUND; HETEROPENTALENE; OXADIAZOLE DERIVATIVE; OXAZOLE DERIVATIVE; PYRROLE DERIVATIVE; THIADIAZOLE DERIVATIVE; THIAZOLE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 4444361567     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.07.132     Document Type: Article
Times cited : (60)

References (50)
  • 26
    • 0141684443 scopus 로고
    • In an unpublished study, we have investigated cyclizations of more than twenty different N,N′-diarylhydrazides and isolated 2,5-diaryl-1,3,4- thiadiazoles in yields heavily scattered in a range of 5% and 95%. For an experimental procedure used in the study, see: C. Tschierske, and D. Girdzinuaite J. Prakt. Chem. 333 1991 135
    • (1991) J. Prakt. Chem. , vol.333 , pp. 135
    • Tschierske, C.1    Girdzinuaite, D.2
  • 29
    • 0003535745 scopus 로고    scopus 로고
    • Cross-Coupling Reactions: A Practical Guide
    • Springer-Verlag New York
    • N. Miyaura Cross-Coupling Reactions: A Practical Guide Topics in Current Chemistry Series 219 2002 Springer-Verlag New York
    • (2002) Topics in Current Chemistry Series 219
    • Miyaura, N.1
  • 44
    • 4444267730 scopus 로고    scopus 로고
    • note
    • An alternative approach for the synthesis of 2-phenylthiophene implementing palladium-catalyzed cross-couplings is a reaction of 2-bromothiophene with a corresponding phenylmetallic reagent. Our investigation revealed that Negishi, Stille, and Suzuki couplings were feasible under conditions of Methods A-C described in Table 1. However, the generality of this approach did not extend to some other heterocycles
  • 45
    • 4444293520 scopus 로고    scopus 로고
    • note
    • Bromination of pyrrole derivatives attempted without sodium acetate buffer led to a significant decomposition of starting material
  • 46
    • 4444346922 scopus 로고    scopus 로고
    • note
    • A representative procedure for selective bromination of 2-arylheteropentalenes: To a stirred homogeneous solution of 2-arylheteropentalene (5.0 mmol) and sodium acetate (10 mmol) in acetic acid (25 mL), bromine (5.0 mmol) was added dropwise via syringe at room temperature over 20-30 min (discoloration of reaction mixture was generally observed during bromine addition). The reaction progress was monitored by TLC or LCMS analyses: upon completion, the reaction mixture was combined with 1 M sodium hydroxide (250 mL) and ethyl acetate (250 mL). The organic layer was separated, washed sequentially with 1 M sodium hydroxide (100 mL) and brine (100 mL), and dried over sodium sulfate. The desired product was obtained by column chromatography on silica gel (eluent: hexanes/ethyl acetate)
  • 47
    • 4444335907 scopus 로고    scopus 로고
    • note
    • If a given 2-aryl-1,3,4-oxa- or thiadiazole is available, bromination under conditions described in Table 2 represents a viable option: several examples of 2-bromo-1,3,4-oxa- and thiadiazoles were isolated in ≥75% yield (reaction temperature 50 A-C for some derivatives).
  • 50
    • 4444351237 scopus 로고    scopus 로고
    • note
    • 4 (0.1 mmol) was added and the mixture was degassed with argon for 2 min after which it was heated under argon to 85 A°C for 3 h. The reaction mixture was combined with 1 M hydrochloric acid (100 mL) and ethyl acetate (200 mL). The organic layer was separated, washed sequentially with 1 M hydrochloric acid (50 mL) and brine (50 mL), and dried over sodium sulfate. The desired product was obtained by column chromatography on silica gel (eluent: hexanes/ethyl acetate)


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