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Volumn 45, Issue 24, 2004, Pages 4661-4664

Six-membered nitrogen ring formation by radical cyclization of trichloroacetamides with enones. A synthetic entry to cis-perhydroisoquinoline- 3,6-diones

Author keywords

Isoquinolines; Madangamines; Nitrogen heterocycles; Radical cyclization; Trichloroacetamides

Indexed keywords

ACETAMIDE DERIVATIVE; HYDROGEN; ISOQUINOLINE DERIVATIVE; NITROGEN;

EID: 2442708756     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.04.104     Document Type: Article
Times cited : (15)

References (47)
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    • In this field, we have used trichloroacetamides as proradical groups with α,β-unsaturated nitriles and esters, alkenes, enol acetates, and silylenol ethers. See, inter alia:
    • In this field, we have used trichloroacetamides as proradical groups with α, β-unsaturated nitriles and esters, alkenes, enol acetates, and silylenol ethers. See, inter alia: Quirante J., Escolano C., Merino A., Bonjoch J. J. Org. Chem. 63:1998;968-976
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    • note
    • 2Ar), 127.4, 127.9, and 128.5 (Ar), 136.7 (ipso-Ar), 167.7 (C-3), 209.3 (C-6). (3a) 28.2 (t), 34.2 (t), 36.6 (d), 54.0 (t), 54.9 (t), 64.0 (t), 108.9 (s), 126.6 (d), 127.8 (d), 128.1 (d), 140.3 (s). (5a) 29.7 (t), 33.5 (d), 39.9 (t), 52.2 (t), 53.7 (t), 92.9 (s), 126.6 (d), 127.6 (d), 128.5 (d), 134.7 (s), 160.7 (s), 210.3 (s). (6a) 26.5 (t), 34.0 (d), 36.3 (t), 51.2 (t), 54.2 (t), 92.9 (s), 127.0 (d), 128.2 (d), 129.0 (d), 130.3 (d), 134.7 (s), 150.0 (d), 161.4 (s), 198.6 (s)
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    • 7 Bu3SnH,AIBN C6H6, rfx, 3 h 8 Me N Bn O O N Bn O O Cl
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    • note
    • Interestingly no cyclization was observed upon the indole 2-position in the radical cyclization of 6c, as has been reported when the radical acceptor is an isolated alkene (see Ref. 10)
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    • Stereoelectronic controls of this type in radical additions to cyclohexenones have been noted earlier: see also Ref. 11
    • Stereoelectronic controls of this type in radical additions to cyclohexenones have been noted earlier: Benko Z., Fraser-Reid B., Mariano P.S., Beckwith A.L.J. J. Org. Chem. 53:1988;2066-2072. see also Ref. 11
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    • note
    • In the same reaction, the corresponding dichloro derivative was isolated in 19% yield


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.