Selective endo and exo iodocyclizations in the synthesis of quinolines and indoles

Organic Letters

Volumn 8, Issue 2, 2006, Pages 243-246

  Hessian, Karl O ^a   Flynn, Bernard L ^a  

^a MONASH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; IODINE; QUINOLINE DERIVATIVE; QUINOLONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CYCLIZATION; INDOLES; IODINE; MOLECULAR STRUCTURE; QUINOLINES; QUINOLONES; STEREOISOMERISM;

EID: 31544481845     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052518j     Document Type: Article

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32. 1H NMR spectra of the crude reaction mixtures. The endo nature of this iodocyclization reaction was based on the characterization of 13a using HMBC (see Supporting Information).
33. Iodocyclizations were also performed in ethanol and acetonitrile using iodine. ICl and N-iodosuccinimide were used as alternative iodonium sources in dichloromethane and acetonitrile.
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37. Evaporating the ethanol from the crude mixture of 16 (R = n-Pr, R′ = H) and adding acetonitrile and heating lead to a 1:2 mixture of indoles 17b and 24a.