Double Mannich reaction with ketones as a route to heterocyclic systems: A mini review

Afsah, Elsayed M.

doi:10.1002/jhet.4809

Journal of Heterocyclic Chem

2024

DOI: 10.1002/jhet.4809

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Double Mannich reaction with ketones as a route to heterocyclic systems: A mini review

Elsayed M. Afsah

Abstract: Double Mannich reaction with ketones is of continuing interest, particularly, in the synthesis of aza‐ and diaza‐heterocycles, alkaloids, and medicinally relevant compounds. The present review deals with the most important literature on the utility of double Mannich reaction in the synthesis and modification of heterocyclic systems.

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Synthesis of Diastereomeric 2,6-bis{[3-(2-Hydroxy-5-substitutedbenzyl)octahydro-1H-benzimidazol-1-yl]methyl}-4-substituted Phenols (R = Me, OMe) by Mannich-Type Tandem Reactions

Quiroga,

Ríos-Motta,

Rivera

2024

Molbank

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The synthesis and characterization of two novel diastereomeric Mannich bases was carried out from the reaction of the cyclic aminal (2R,7R,11S,16S)-1,8,10,17-tetraazapentacyclo[8.8.1.1.8,170.2,70.11,16]icosane 1 and p-cresol 2a and 4-methoxyphenol 2b in a water/dioxane mixture. The title compounds (4a–b) are interesting because bearing two 3-(2-hydroxy-5-substitutedbenzyl)octahydro-1H-benzimidazol-1-yl]methyl} substituents joined to an arenol ring. The formation of these new Mannich bases in the reaction mixture can be explained by aminomethylation of previously reported di-Mannich base 2,2′-((hexahydro-1H-benzo[d]imidazole-1,3(2H)-diyl)bis(methylene))bis(4-substituentphenol) 3a–b. NMR analysis demonstrated that compounds 4a–b were formed as diastereomeric mixtures. Subsequent experiments revealed that at longer reaction times, the percentage yield of these new products increased considerably (yield percentages up to 22–27%), suggesting a nucleophilic competition between the p-substituted phenols and Mannich bases of type 3 for aminal 1.

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Synthesis of Diastereomeric 2,6-bis{[3-(2-Hydroxy-5-substitutedbenzyl)octahydro-1H-benzimidazol-1-yl]methyl}-4-substituted Phenols (R = Me, OMe) by Mannich-Type Tandem Reactions

Quiroga,

Ríos-Motta,

Rivera

2024

Molbank

View full text Add to dashboard Cite

show abstract

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Double Mannich reaction with ketones as a route to heterocyclic systems: A mini review

Cited by 1 publication

References 116 publications

Synthesis of Diastereomeric 2,6-bis{[3-(2-Hydroxy-5-substitutedbenzyl)octahydro-1H-benzimidazol-1-yl]methyl}-4-substituted Phenols (R = Me, OMe) by Mannich-Type Tandem Reactions

Synthesis of Diastereomeric 2,6-bis{[3-(2-Hydroxy-5-substitutedbenzyl)octahydro-1H-benzimidazol-1-yl]methyl}-4-substituted Phenols (R = Me, OMe) by Mannich-Type Tandem Reactions

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