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Paper | Regular issue | Vol 100, No. 10, 2020, pp.1613-1622
Published online, 12th August, 2020
DOI: 10.3987/COM-20-14314
A One-Pot Four-Component Procedure for the Synthesis of Dispiro[tetrahydroquinoline-bis(2,2-dimethyl-1,3-dioxane-4,6-dione)] Derivatives

Zhaohui Xu,* Yexuan Tang, Qiang Xiao, and Chuanwen Liao*

*Department of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, P.R. China.

Abstract

A simple and efficient procedure for the diastereoselective synthesis of dispiro[tetrahydroquinoline-bis(2,2-dimethyl-1,3-dioxane-4,6-dione)] derivatives through one-pot four-component reaction of aromatic aldehydes, 2,2-dimethyl-1,3-dioxane-4,6-dione, arylamines and acetone in the presence of potassium dihydrogen phosphate (KDP) is described. The procedure involves initial Knoevenagel reaction, followed by Diels-Alder, Michael additon and intramolecular reactions. The main advantages of the protocol are the high isolated yields, broad substrate scope, mild conditions, and easy operation.