Affiliation:
1. School of Pharmaceutical Sciences, National Demonstration Center for Experimental Ethnopharmacology Education South-Central University of Nationalities Wuhan 430074 People's Republic of China
Abstract
AbstractAn acetic acid‐catalyzed [2+2+1+1] cycloaddition of 1,3,5‐triazinanes with methylene compounds was developed. This protocol provides an access to hexahydropyrimidines (HHPs) (25 examples) in 35–99% yields under mild conditions in 2 hours. The potential application of this method was demonstrated by gram‐scale synthesis. Preliminary mechanistic investigation was conducted to elucidate the possible mechanism. This work represents the yet unknown example of [2+2+1+1] cycloaddition reaction between 1,3,5‐triazinanes and active methylene compounds.
Funder
National Natural Science Foundation of China
Cited by
4 articles.
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1. Additive-Free Construction of Tetrahydropyrimidine Skeleton by using 1,3,5-Triazinane as Four-Atom Synthon;The Journal of Organic Chemistry;2024-06-18
2. Palladium-Catalyzed Cycloaddition Reactions of π–Allylpalladium 1,4-Dipoles with 1,3,5-Triazinanes: Access to Hexahydropyrimidines, 1,3-Oxazinanes, and 1,5-Diazocanes;The Journal of Organic Chemistry;2024-06-07
3. Reaction of 1,3,5-Triazinanes with Phosphoryl Diazomethanes: Access to 5-Phosphoryl-1,2,3,4-tetrahydropyrimidines;Organic Letters;2024-04-17
4. Substituent-controlled divergent cyclization reactions of benzo[c][1,2]dithiol-3-ones and hexahydro-1,3,5-triazines;Organic Chemistry Frontiers;2024