Synthesis 2016; 48(04): 547-556
DOI: 10.1055/s-0035-1561296
paper
© Georg Thieme Verlag Stuttgart · New York

‘On-Water’ Multicomponent Reaction for the Diastereoselective Synthesis of Functionalized Tetrahydropyridines and Mechanistic Insight

Naisargee Parikh, Sudipta Raha Roy, Kapileswar Seth, Asim Kumar, Asit K. Chakraborti*
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Publication History

Received: 30 July 2015

Accepted after revision: 23 November 2015

Publication Date:
29 December 2015 (eFirst)

Abstract

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.

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