Synthesis of Substituted Isoquinolines by Electrophilic Cyclization of Iminoalkynes

The tert-butylimines of o-(1-alkynyl)benzaldehydes and analogous pyridinecarbaldehydes have been cyclized under very mild reaction conditions in the presence of I2, ICl, PhSeCl, PhSCl, and p-O2NC6H4SCl to give the corresponding halogen-, selenium-, and sulfur-containing disubstituted isoquinolines a...

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Published in:Journal of organic chemistry 2002-05, Vol.67 (10), p.3437-3444
Main Authors: Huang, Qinhua, Hunter, Jack A, Larock, Richard C
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Language:English
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Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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cited_by cdi_FETCH-LOGICAL-a445t-c51913767837fc0919e3a25a366d604d0d8aac88245f67179a99e1b73a0cfea93
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description The tert-butylimines of o-(1-alkynyl)benzaldehydes and analogous pyridinecarbaldehydes have been cyclized under very mild reaction conditions in the presence of I2, ICl, PhSeCl, PhSCl, and p-O2NC6H4SCl 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 °C.
doi_str_mv 10.1021/jo020020e
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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. 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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
title Synthesis of Substituted Isoquinolines by Electrophilic Cyclization of Iminoalkynes
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