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Redox-Annulations of Cyclic Amines with 2-(2-Oxoethyl)malonates. | LitMetric

Redox-Annulations of Cyclic Amines with 2-(2-Oxoethyl)malonates.

Org Lett

Center for Heterocyclic Compounds, Department of Chemistry , University of Florida, Gainesville , Florida 32611 , United States.

Published: July 2018

AI Article Synopsis

  • Amines like 1,2,3,4-tetrahydroisoquinoline react with 2-(2-oxoethyl)malonates in a redox-neutral way when catalyzed by benzoic acid.
  • This reaction results in the formation of a fully saturated five-membered ring.
  • The products are similar to natural compounds such as crispine A and harmicine.

Article Abstract

Amines such as 1,2,3,4-tetrahydroisoquinoline undergo redox-neutral annulations with 2-(2-oxoethyl)malonates in the presence of catalytic amounts of benzoic acid. These reactions install a fully saturated five-membered ring and provide access to structures closely related to the natural products crispine A and harmicine.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6060407PMC
http://dx.doi.org/10.1021/acs.orglett.8b01642DOI Listing

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