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β‐Ketodithioesters as Versatile Building Blocks for the Diversity Oriented Synthesis of Thioamides, α‐Allylated‐Thioesters and Ketoamides
Author(s) -
Chanu Irom Harimala,
Devi Laishram Momota,
Singh Thokchom Prasanta,
Singh Sarangthem Joychandra,
Singh Rajkumar Romeshkumar,
Mukherjee Singh Okram
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202001807
Subject(s) - knoevenagel condensation , chemistry , electrophile , nucleophile , allyl bromide , piperidine , condensation , base (topology) , bromide , combinatorial chemistry , organic chemistry , condensation reaction , catalysis , mathematical analysis , physics , mathematics , thermodynamics
When β ‐ketodithioesters ( β ‐KDEs) are treated with various electrophiles in multi‐component reactions, three types of highly substituted and densely functionalized reactive intermediates are generated in good yields. Dual role of piperidine as base and nucleophile in Knoevenagel condensation reactions of aromatic aldehydes and β ‐ketodithioesters has been observed in our investigations. Trisubstituted ( Z )‐prop‐2‐en‐1‐ones have been obtained stereoselectively as a result of these condensation reactions. β ‐KDEs were further utilized in allylation reactions with allyl bromide and alkylamines leading to allylated β ‐ketodithioestersand allylated β ‐ketoamides in good yields.