Affiliation:
1. Saint Petersburg State University
Abstract
Hitherto undescribed 3-unsubstituted tetrahydroisoquinolonic acids (isolated as their respective methyl esters) were accessed for the first time by the uncatalyzed, thermally promoted Castagnoli–Cushman reaction (CCR) of homophthalic anhydride (HPA) and a series of 1,3,5-triazinanes. The moderate yields observed in some cases are most likely associated with a persistent impurity also formed in these reactions. The new scaffold is expected to find novel medicinal utility (compared to the traditional CCR adducts) because it lacks a substituent at the 3-position.
Funder
Russian Science Foundation
Subject
Organic Chemistry,Catalysis
Cited by
16 articles.
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1. Reaction of 1,3,5-Triazinanes with Phosphoryl Diazomethanes: Access to 5-Phosphoryl-1,2,3,4-tetrahydropyrimidines;Organic Letters;2024-04-17
2. The Castagnoli–Cushman Reaction;Molecules;2023-03-15
3. Synthesis of 3,4-dihydroisoquinolin-1(2H)-one derivatives and their antioomycete activity against the phytopathogen Pythium recalcitrans;RSC Advances;2023
4. Synthesis of Chromeno[2,3-d]pyrimidin-5-one Derivatives from 1,3,5-Triazinanes via Two Different Reaction Pathways;The Journal of Organic Chemistry;2022-01-11
5. Synthesis of α‐Amino Tertiary Alkylperoxides by Lewis Acid‐Catalyzed Peroxidation of 1,3,5‐Triazines;Chemistry – An Asian Journal;2021-09-16