N-Methylimidazole Promotes the Reaction of Homophthalic Anhydride with Imines

[Image: see text] The addition of N-methylimidazole (NMI) to the reaction of homophthalic anhydride with imines such as pyridine-3-carboxaldehyde-N-trifluoroethylimine (9) reduces the amount of elimination byproduct and improves the yield of the formal cycloadduct, tetrahydroisoquinolonic carboxylat...

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Autores principales: Liu, Jian, Wang, Zheng, Levin, Aaron, Emge, Thomas J., Rablen, Paul R., Floyd, David M., Knapp, Spencer
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4136697/
https://www.ncbi.nlm.nih.gov/pubmed/25036978
http://dx.doi.org/10.1021/jo501316m
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author Liu, Jian
Wang, Zheng
Levin, Aaron
Emge, Thomas J.
Rablen, Paul R.
Floyd, David M.
Knapp, Spencer
author_facet Liu, Jian
Wang, Zheng
Levin, Aaron
Emge, Thomas J.
Rablen, Paul R.
Floyd, David M.
Knapp, Spencer
author_sort Liu, Jian
collection PubMed
description [Image: see text] The addition of N-methylimidazole (NMI) to the reaction of homophthalic anhydride with imines such as pyridine-3-carboxaldehyde-N-trifluoroethylimine (9) reduces the amount of elimination byproduct and improves the yield of the formal cycloadduct, tetrahydroisoquinolonic carboxylate 10. Carboxanilides of such compounds are of interest as potential antimalarial agents. A mechanism that rationalizes the role of NMI is proposed, and a gram-scale procedure for the synthesis and resolution of 10 is also described.
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spelling pubmed-41366972015-07-18 N-Methylimidazole Promotes the Reaction of Homophthalic Anhydride with Imines Liu, Jian Wang, Zheng Levin, Aaron Emge, Thomas J. Rablen, Paul R. Floyd, David M. Knapp, Spencer J Org Chem [Image: see text] The addition of N-methylimidazole (NMI) to the reaction of homophthalic anhydride with imines such as pyridine-3-carboxaldehyde-N-trifluoroethylimine (9) reduces the amount of elimination byproduct and improves the yield of the formal cycloadduct, tetrahydroisoquinolonic carboxylate 10. Carboxanilides of such compounds are of interest as potential antimalarial agents. A mechanism that rationalizes the role of NMI is proposed, and a gram-scale procedure for the synthesis and resolution of 10 is also described. American Chemical Society 2014-07-18 2014-08-15 /pmc/articles/PMC4136697/ /pubmed/25036978 http://dx.doi.org/10.1021/jo501316m Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Liu, Jian
Wang, Zheng
Levin, Aaron
Emge, Thomas J.
Rablen, Paul R.
Floyd, David M.
Knapp, Spencer
N-Methylimidazole Promotes the Reaction of Homophthalic Anhydride with Imines
title N-Methylimidazole Promotes the Reaction of Homophthalic Anhydride with Imines
title_full N-Methylimidazole Promotes the Reaction of Homophthalic Anhydride with Imines
title_fullStr N-Methylimidazole Promotes the Reaction of Homophthalic Anhydride with Imines
title_full_unstemmed N-Methylimidazole Promotes the Reaction of Homophthalic Anhydride with Imines
title_short N-Methylimidazole Promotes the Reaction of Homophthalic Anhydride with Imines
title_sort n-methylimidazole promotes the reaction of homophthalic anhydride with imines
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4136697/
https://www.ncbi.nlm.nih.gov/pubmed/25036978
http://dx.doi.org/10.1021/jo501316m
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