Synthesis of 1,2-Dihydroisoquinolines via Rhenium-catalyzed Tandem Cyclization and Nucleophilic Addition of 2-(1-Alkynyl)arylaldimines

A synthetic method for 1,2-dihydroisoquinolines via the 6-endo-dig cyclization of 2-alkynylaldimines and nucleophilic addition has been developed. When the 2-alkynylaldimines were reacted with various nucleophiles such as nitromethane, dimethyl malonate, phenylacetylene, hydrosilane, allylstannane,...

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Published inChemistry letters Vol. 47; no. 6; pp. 753 - 755
Main Authors Umeda, Rui, Ishida, Tetsuya, Nakagawa, Yota, Inoue, Mitsuru, Yajima, Tatsuo, Nishiyama, Yutaka
Format Journal Article
LanguageEnglish
Published TOKYO Chemical Soc Japan 05.06.2018
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
3-COMPONENT REACTION
NAPHTHYRIDINES
EFFICIENT ROUTE
2-ALKYNYLBENZALDEHYDES
METAL-CARBONYLS
ALKYNYLARYLALDIMINES
ISOQUINOLINE
AMINES
2-Alkynylaldimines
Rhenium
CONCISE SYNTHESIS
1,2-Dihydroisoquinolines
WATER
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Summary:A synthetic method for 1,2-dihydroisoquinolines via the 6-endo-dig cyclization of 2-alkynylaldimines and nucleophilic addition has been developed. When the 2-alkynylaldimines were reacted with various nucleophiles such as nitromethane, dimethyl malonate, phenylacetylene, hydrosilane, allylstannane, and ketene silyl acetal in the presence of a rhenium catalyst, the corresponding 1,2-dihydroisoquinolines were obtained in moderate to good yields.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.180200