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Volumn 133, Issue 30, 2011, Pages 11466-11469

Direct synthesis of fluorescent 1,3a,6a-triazapentalene derivatives via click-cyclization-aromatization cascade reaction

Author keywords

[No Author keywords available]

Indexed keywords

CASCADE REACTIONS; DIRECT SYNTHESIS; FLUORESCENT CHROMOPHORES; FLUORESCENT PROPERTY; FUSED-RING SYSTEM; VERSATILE METHODS;

EID: 79960879625     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja203917r     Document Type: Article
Times cited : (53)

References (33)
  • 1
    • 0041670478 scopus 로고    scopus 로고
    • Shinar, J., Ed.; Springer: New York.
    • Shinar, J., Ed. Organic Light-Emitting Devices; Springer: New York, 2004.
    • (2004) Organic Light-Emitting Devices
  • 3
    • 79960856554 scopus 로고    scopus 로고
    • Willardson, R. K.; Weber, E.; Mueller, G.; Sato, Y.; Semiconductors and Semimetals Series; Academic Press: New York.
    • Willardson, R. K.; Weber, E.; Mueller, G.; Sato, Y. Electroluminescence 1; Semiconductors and Semimetals Series; Academic Press: New York, 1999.
    • (1999) Electroluminescence 1
  • 25
    • 84855669869 scopus 로고    scopus 로고
    • Treatment of 3-chloro-1,2-propanediol with sodium azide in water afforded the corresponding azidodiol, which was directly converted to 4a in 82% yield. The multigram-scale preparation of 4a was actually conducted several times without incident. The microscopic observation of thermolytic behavior of 4a (neat) by melting point apparatus revealed that 4a decomposes and partially volatilizes at 92 °C. Although we found that a solution of 4a in 1,4-dioxane is stable enough to be heated to 100 °C for 2 h, manipulating 4a at high temperature is not recommended. Further investigation about safety is currently underway.
    • Treatment of 3-chloro-1,2-propanediol with sodium azide in water afforded the corresponding azidodiol, which was directly converted to 4a in 82% yield. The multigram-scale preparation of 4a was actually conducted several times without incident. The microscopic observation of thermolytic behavior of 4a (neat) by melting point apparatus revealed that 4a decomposes and partially volatilizes at 92 °C. Although we found that a solution of 4a in 1,4-dioxane is stable enough to be heated to 100 °C for 2 h, manipulating 4a at high temperature is not recommended. Further investigation about safety is currently underway.
  • 26
    • 79960851112 scopus 로고    scopus 로고
    • The use of 2,6-lutidine and DBU as bases did not give 1b because they reacted with 4a faster than the click reaction. The yield of 1b was reduced to 66% when diisopropylethylamine was used. The amount of triethylamine could be reduced to 2.0 equiv without a significant loss of yield.
    • The use of 2,6-lutidine and DBU as bases did not give 1b because they reacted with 4a faster than the click reaction. The yield of 1b was reduced to 66% when diisopropylethylamine was used. The amount of triethylamine could be reduced to 2.0 equiv without a significant loss of yield.
  • 27
    • 79960856334 scopus 로고    scopus 로고
    • The isolated yield of 1b was reduced to 71% because a part of 1b was decomposed to blue product, which strongly adsorbed on silica gel, during column chromatography.
    • The isolated yield of 1b was reduced to 71% because a part of 1b was decomposed to blue product, which strongly adsorbed on silica gel, during column chromatography.
  • 28
    • 79960888569 scopus 로고    scopus 로고
    • Attempts for isolating the triazolium ion 5b were unsuccessful. Therefore, the structure of 5b was determined on the basis of the correlation with triazoium ion 5c, which was easily obtained by a similar click reaction of 4b with 3c.
    • Attempts for isolating the triazolium ion 5b were unsuccessful. Therefore, the structure of 5b was determined on the basis of the correlation with triazoium ion 5c, which was easily obtained by a similar click reaction of 4b with 3c.
  • 29
    • 79960849084 scopus 로고    scopus 로고
    • Treatment of 1e with 1.0 equiv of lithium hydroxide afforded lithium carboxylate 1o in quantitative yield. The amide 1p was prepared by the coupling of 1o with glycine ethyl ester hydrochloride by the combined action of EDCI and DMAP in DMF.
    • Treatment of 1e with 1.0 equiv of lithium hydroxide afforded lithium carboxylate 1o in quantitative yield. The amide 1p was prepared by the coupling of 1o with glycine ethyl ester hydrochloride by the combined action of EDCI and DMAP in DMF.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.