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Volumn , Issue 15, 2008, Pages 2331-2333

Regioselective synthesis of functionalized 3-(methylthio)phenols by the first formal [3+3] cyclocondensations of 1,3-bis(trimethylsilyloxy)-1,3- butadienes with 1,1-bis(methylthio)-1-en-3-ones

Author keywords

Arenes; Cyclizations; Regioselectivity; Silyl enol ethers

Indexed keywords

1,1 BIS(METHYLTHIO) 1 EN 3 ONE DERIVATIVE; 1,3 BIS(SILYL ENOL ETHER DERIVATIVE); 1,3 BIS(TRIMETHYLSILYLOXY) 1,3 BUTADIENE DERIVATIVE; 1,3 BUTADIENE DERIVATIVE; 3 (METHYLTHIO)PHENOL DERIVATIVE; ETHER DERIVATIVE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 52949142239     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1077977     Document Type: Article
Times cited : (15)

References (29)
  • 21
    • 0036200130 scopus 로고    scopus 로고
    • For a review of 1,3-bis(silyl enol ethers) in general, see
    • For a review of 1,3-bis(silyl enol ethers) in general, see: Langer, P. Synthesis 2002, 441.
    • (2002) Synthesis , pp. 441
    • Langer, P.1
  • 22
    • 33947178424 scopus 로고    scopus 로고
    • For a review of [3+3] cyclocondensations of 1,3-bis(silyl enol ethers) with 1,3-dielectrophiles, see: Feist, H.; Langer, P. Synthesis 2007, 327.
    • For a review of [3+3] cyclocondensations of 1,3-bis(silyl enol ethers) with 1,3-dielectrophiles, see: Feist, H.; Langer, P. Synthesis 2007, 327.
  • 28
    • 52949132931 scopus 로고    scopus 로고
    • Typical Procedure: Synthesis of Ethyl 4-Ethyl-6-hydroxy-3-methyl-2, methylthio)benzoate(4b) To a solution of 2b (0.190 g, 1.0 mmol) and 3b (0.549 g, 2.0 mmol) in CH2Cl2 (2 mL) was added TiCl4 (0.11 mL, 1.0 mmol) at -78°C under argon. The temperature of the reaction mixture was allowed to rise to 20°C during 14 h, and an aq HCl solution (10, 10 mL) was added. The organic layer was separated, and the aqueous layer was extracted with CH2Cl2 (3 x 10 mL, The combined organic layers were dried (Na2SO4, filtered, and concentrated in vacuo. After column chromatography (SiO2, heptane-EtOAc, 10:1, 4b was obtained as a colorless solid (227 mg, 89, mp 120-121°C; Rf, 0.39 (heptane-EtOAc, 3:1, 1H NMR (250 MHz, CDCl3, δ, 9.06 (s, 1 H, OH, 6.78 (s, 1 H, ArH, 4.43 q, 3J, 7.1 Hz, 2 H, OCH2
    • 3S (254.10): C, 61.39; H, 7.13. Found: C, 61.35; H, 7.27.
  • 29
    • 52949093434 scopus 로고    scopus 로고
    • CCDC-685823 contains all crystallographic details of this publication and is available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; or deposit@ccdc.cam.ac.uk.
    • CCDC-685823 contains all crystallographic details of this publication and is available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; or deposit@ccdc.cam.ac.uk.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.