Synthesis of 2,4-diiodoquinolines via the photochemical cyclization of o-alkynylaryl isocyanides with iodine

Journal of Organic Chemistry

Volumn 76, Issue 4, 2011, Pages 1163-1166

  Mitamura, Takenori ^a   Ogawa, Akiya ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GOOD YIELD; INTRAMOLECULAR CYCLIZATIONS; ISOCYANIDES; METAL-CATALYZED CROSS-COUPLING REACTIONS; PHOTO-IRRADIATION;

CYANIDES; INDUSTRIAL CHEMICALS; IODINE; TRANSITION METALS;

CYCLIZATION;

2,4 DIIODOQUINOLINE; CYANIDE; IODINE; QUINOLONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; CYCLIZATION; PHOTOCHEMISTRY; SYNTHESIS;

CYANIDES; CYCLIZATION; HYDROCARBONS, IODINATED; IODINE; MOLECULAR STRUCTURE; PHOTOCHEMISTRY; QUINOLINES;

EID: 79951638034     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1021772     Document Type: Article

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59. To clarify the reaction pathway, we also conducted the photochemical reaction of isocyanide 1a with tributyltin hydride, which has excellent carbon-radical-capturing ability. The reaction afforded 3-phenylquinoline in 76% yield, and 2-tributylstannyl-3-phenyl quinoline was not obtained. These results strongly suggest that the photochemical reaction of o-alkynylaryl isocyanides follows the aza-Bergman cyclization via the formation of 2,4-biradical species.
60. 1H NMR spectra, respectively. Both peaks indicated the formation of the corresponding 2-hydroquinolines by the elimination of iodide.