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Heterocycles
Volumn 85, Issue 1, 2012, Pages 35-41
First synthesis of 2-heteroarylazulenes by the electrophilic substitution of azulene with triflate of N-containing heterocycles
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EID: 84855385021     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-11-12373     Document Type: Article
Times cited : (16)
References (36)
  • 1
    • 0000829582 scopus 로고
    • Azulene
    • 4th ed. (Ed.: H. Kropf), Georg Thieme, Stuttgart, Germany, part 2c
    • K.-P. Zeller, "Azulene", in Houben-Weyl, Methoden der Organischen Chemie, 4th ed. (Ed.: H. Kropf), Georg Thieme, Stuttgart, Germany, 1985, vol. V, part 2c, pp. 127-418.
    • (1985) Houben-Weyl, Methoden der Organischen Chemie , vol.V , pp. 127-418
    • Zeller, K.-P.1
  • 33
    • 84855378918 scopus 로고    scopus 로고
    • 3N were added to the residue and the mixture was refluxed for 2 h. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel to give the corresponding 6-substituted-1,3-di(methylthio)azulenes 1b, 1c and 1d, respectively (R = H, 98% yield; R = tert-Bu, 96% yield; R = OMe, 97% yield
    • 3N were added to the residue and the mixture was refluxed for 2 h. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel to give the corresponding 6-substituted-1,3-di(methylthio)azulenes 1b, 1c and 1d, respectively (R = H, 98% yield; R = tert-Bu, 96% yield; R = OMe, 97% yield).
    • General Procedure for the Synthesis of 6-substituted-1,3-di(methylthio) azulenes 1b, 1c and 1d
  • 34
    • 84855408636 scopus 로고    scopus 로고
    • 2. After the resulting solution was stirred for 1-3 h at 0 °C, the solvent was removed in vacuo. The products were purified by column chromatography on silica gel to give the corresponding 6-dimethylamino-1,3-di(methylthio)-2-(dihydroheteroaryl)azulenes 2-7 (yield of the products is shown in Table 2
    • 2. After the resulting solution was stirred for 1-3 h at 0 °C, the solvent was removed in vacuo. The products were purified by column chromatography on silica gel to give the corresponding 6-dimethylamino-1,3-di(methylthio)-2-(dihydroheteroaryl)azulenes 2-7 (yield of the products is shown in Table 2).
    • General Procedure for the Synthesis of 6-dimethylamino-1,3-di(methylthio) -2-(dihydroheteroaryl)azulenes 2-7
  • 35
    • 84855370452 scopus 로고    scopus 로고
    • To a solution of 2-7 in MeOH (or i-PrOH) was added potassium hydroxide. After the resulting mixture was refluxed for 5-17 h, the reaction mixture was poured into brine and extracted with EtOAc. The crude product was purified by column chromatography on alumina to afford corresponding 6-dimethylamino-1,3- di(methylthio)-2-heteroarylazulenes 8-11 (the yield of the products is shown in Table 3
    • General procedure for the preparation of 6-dimethylamino-1,3- di(methylthio)-2-heteroarylazulenes 8-11. To a solution of 2-7 in MeOH (or i-PrOH) was added potassium hydroxide. After the resulting mixture was refluxed for 5-17 h, the reaction mixture was poured into brine and extracted with EtOAc. The crude product was purified by column chromatography on alumina to afford corresponding 6-dimethylamino-1,3-di(methylthio)-2-heteroarylazulenes 8-11 (the yield of the products is shown in Table 3).
    • General Procedure for the Preparation of 6-dimethylamino-1,3- di(methylthio)-2-heteroarylazulenes 8-11

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.