N-Methylimidazole Promotes the Reaction of Homophthalic Anhydride with Imines | Zendy

Jian Liu | Zendy; Zheng Wang | Zendy; Aaron Levin | Zendy; Thomas J. Emge | Zendy; Paul R. Rablen | Zendy; David Floyd | Zendy; Spencer Knapp | Zendy

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N-Methylimidazole Promotes the Reaction of Homophthalic Anhydride with Imines

Author(s) -

Jian Liu,

Zheng Wang,

Aaron Levin,

Thomas J. Emge,

Paul R. Rablen,

David Floyd,

Spencer Knapp

Publication year - 2014

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo501316m

Subject(s) - chemistry , yield (engineering) , pyridine , carboxylate , combinatorial chemistry , organic chemistry , metallurgy , materials science

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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