"On-Water' Multicomponent Reaction for the Diastereoselective Synthesis of Functionalized Tetrahydropyridines and Mechanistic Insight

An ecofriendly approach for the synthesis of highly substituted tetrahydropyridines by an on-water' multicomponent reaction has been demonstrated. The use of water as the reaction medium is essential under the catalytic influence of a surfactant. The use of a variety of anionic, cationic, and n...

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Published inSynthesis (Stuttgart) Vol. 48; no. 4; pp. 547 - 556
Main Authors Parikh, Naisargee, Roy, Sudipta Raha, Seth, Kapileswar, Kumar, Asim, Chakraborti, Asit K.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 16.02.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ROOM-TEMPERATURE
SOLVENT-FREE CONDITIONS
ONE-POT SYNTHESIS
ORGANIC-REACTIONS
EFFICIENT SYNTHESIS
tetrahydropyridines
AROMATIC-ALDEHYDES
CATALYZED ONE-POT
PIPERIDINE SCAFFOLDS
GREEN CHEMISTRY
multicomponent reaction
diastereoselective
on-water
MEDICINAL CHEMISTS
surfactant
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Summary:An ecofriendly approach for the synthesis of highly substituted tetrahydropyridines by an on-water' multicomponent reaction has been demonstrated. The use of water as the reaction medium is essential under the catalytic influence of a surfactant. The use of a variety of anionic, cationic, and non-ionic surfactants in water was examined and the reaction was successfully catalyzed by anionic surfactants sodium dioctyl sulfosuccinate (SDOSS) and sodium dodecyl sulfate (SDS), with the former being superior. The use of an organic solvent together with a catalytic amount of sodium dioctyl sulfosuccinate to form homogeneous conditions afforded inferior yields and highlighted the specific role of water through the creation of microreactors at the water surfactant interface. A mechanistic insight for the five-component reaction leading to the formation of tetrahydropyridines is provided invoking a tandem inter- and intramolecular Mannich reaction pathway.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0035-1561296