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Amino Acid‐Based Dithiocarbamates as Efficient Intermediates for Diversity‐Oriented Synthesis of Thiazoles
Author(s) -
Ziyaei Halimehjani Azim,
Khalesi Maryam,
Breit Bernhard
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001050
Subject(s) - chemistry , organic chemistry , adduct , reagent , halide , combinatorial chemistry
Amino acid‐based dithiocarbamates were introduced as efficient intermediates for the synthesis of a diverse library of novel di‐ and tri‐substituted thiazoles via condensation with various reagents such as anhydrides, acyl halides, benzene sulfonyl chloride, trifluoromethanesulfonic anhydride, chloroethyl formate, and diethyl chlorophosphate. The utilities of adducts in further organic synthesis were confirmed by Sonogashira and oxidation reactions. In addition, reaction of aspartic acid‐based dithiocarbamates with anhydrides affords the corresponding fused 6,6a‐dihydrofuro[3,2‐ d ]thiazol‐5(3a H )‐ones diastereoselectively in excellent yields.