Open AccessA Study on N-Substituted Nortropinone Synthesis using Acetone Equivalents
Author(s) -
Jae Min Song,
Song Mi Bae,
S.K. Cho,
Jong Hyun Cho,
DaiIl Jung
Publication year - 2020
Publication title -
asian journal of chemistry/asian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.145
H-Index - 34
eISSN - 0975-427X
pISSN - 0970-7077
DOI - 10.14233/ajchem.2020.22537
Subject(s) - acetone , chemistry , dicarboxylic acid , tetrahydrofuran , yield (engineering) , organic chemistry , materials science , solvent , metallurgy
Robinson′s synthesis has long been a classic in organic chemistry due to its simplicity and impact inthe industry. Various modifications have been made to improve the system. Among them, replacingacetone with more acidic chemical equivalents such as calcium dicarboxylic acid or ethyl dicarboxylicacetone improved the yield. In line with this trend, our group previously reported the synthesis ofmono- and di-N-substituted tropinone derivatives from the one-pot reaction of 2,5-dimethoxytetrahydrofuran and various amines with acetonedicarboxylic acid in the presence of HCl and water atroom temperature. In this study, the synthesis with acetone instead of acetone-dicarboxylic acid wasexamined. Mono- and di-N-substituted nortropinones were prepared in higher yields in all cases althoughthere were extent to which yields increased depending on the nature of substituents