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Rhodanine‐Furan Bis‐Heterocyclic Frameworks Synthesis via Green One‐Pot Sequential Six‐Component Reactions: A Synthetic and Computational Study
Author(s) -
Hooshmand Seyyed Emad,
Ghadari Rahim,
Mohammadian Reza,
Shaabani Ahmad,
Khavasi Hamid Reza
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201903361
Subject(s) - chemistry , cycloaddition , furan , rhodanine , combinatorial chemistry , adduct , michael reaction , cascade reaction , catalysis , organic chemistry
Combinatorial construction of a drug‐like library of novel rhodanine‐furan bis ‐heterocyclic scaffolds has been demonstrated through a novel one‐pot sequential six‐component reaction in water under ultrasound irradiation with 100% atom economy. The process is a sequence of tandem Michael reactions followed by domino cycloaddition/zwitterionic adduct formation/Mumm rearrangement/[1+4] cycloaddition processes, involving diverse primary amines, carbon disulfide, maleic anhydride, dialkyl acetylenedicarboxylates and various isocyanides. No catalyst was required, but the use of aqueous two‐phase (on water) conditions was critical. Docking and molecular dynamics calculations performed on human aldose reductase suggest that the bis ‐heterocyclic frameworks formed may be useful inhibitors of this enzyme.