Synthesis of quinoline-2-thiones via tandem indium(III)-promoted friedel-crafts alkenylation-cyclization of 2-alkynylphenyl isothiocyanates

Organic Letters

Volumn 9, Issue 26, 2007, Pages 5513-5516

  Otani, Takashi ^a   Kunimatsu, Shinichi ^a   Nihei, Hiroshi ^a   Abe, Yuko ^a   Saito, Takao ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; INDIUM; ISOTHIOCYANIC ACID DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; CHEMISTRY; CYCLIZATION;

ALKENES; CYCLIZATION; INDIUM; ISOTHIOCYANATES; QUINOLINES;

EID: 38349125100     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7024668     Document Type: Article

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38. 3 at 120°C for 4 h gave 3-butyl-4-(2,5-dimethoxyphenyl)-2(1H)-quinolinethione in 53% yield.
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45. 2-tert-Butyl-1,4-dimethoxybenzene was actually isolated in 20% yield (Table 2, entry 2).
46. 3 revealed an initial formation of 2,5-dimethoxy-1-[(1Z)-3,3-dimethyl-1-phenyl-1-butenyl]benzene and its subsequent decomposition leading to 2-tert-butyl-1,4-dimethoxybenzene and 1-(2,5-dimethoxyphenyl)-1-phenylethene, albeit in low yield. These results support the pathways 1c to C via A and B in Scheme 2.