Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 67, Issue 10, Pages 3437-3444Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo020020e
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The tert-butylimines of o-(1-alkynyl)benzaldehydes and analogous pyridinecarbaldehydes have been cyclized under very mild reaction conditions in the presence Of I-2, ICI, PhSeCl, PhSCl, and P-O-2-NC6H4SCl to give the corresponding halogen-, selenium-, and sulfur-containing disubstituted isoquinolines and naphthyridines, respectively. This methodology accommodates a variety of iminoalkynes and affords the anticipated heterocycles in moderate to excellent yields. Monosubstituted isoquinolines and naphthyridines have been synthesized by the metal-catalyzed ring closure of these same iminoalkynes. The silver-catalyzed ring closure is highly effective in cyclizing aryl-, alkenyl-, and alkyl-substituted iminoalkynes at 50 degreesC.
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