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β‐Cyclodextrin Monosulphonic Acid Promoted Multicomponent Synthesis of 1,8‐Dioxodecahydroacridines in Water
Author(s) -
Madankumar Natarajan,
Pitchumani Kasi
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201802244
Subject(s) - chemistry , catalysis , environmentally friendly , green chemistry , reusability , dimedone , organic chemistry , cyclodextrin , ammonium chloride , chloride , nuclear chemistry , reaction mechanism , ecology , software , computer science , biology , programming language
A simple and efficient route for the synthesis of 1,8‐dioxodecahydroacridine derivatives in water is described using β‐cyclodextrin monosulphonic acid (prepared readily from β‐cyclodextrin obtained by enzymatic degradation of starch and chlorosulphonic acid), as an environmentally friendly acid catalyst. In this one‐pot method, 1,8‐dioxodecahydroacridine derivatives (19 compounds) are synthesized from dimedone, ammonium chloride and aromatic aldehydes in high yields (upto 94 %). All the synthesized compounds are extensively characterized by 1 H and 13 C‐NMR, ESI‐MS and also by their melting points. A plausible mechanism involving a multifunctional role for β‐cyclodextrin monosulphonic acid is proposed. The other key benefits and green credentials of this protocol are nitrogen assimilation (formation of organic nitrogen compounds from ammonium chloride in laboratory), use of water which is an environmentally benign solvent, solid acid catalyst, easy workup, reusability upto five times, milder reaction conditions and broad substrate scope.