Tandem Alkylation/Michael Addition Reaction of Dithiocarbamic Acids with Alkyl γ-Bromocrotonates: Access to Functionalized 1,3-Thiazolidine-2-thiones

Synthesis ◽  
2021 ◽  
Author(s):  
Azim Ziyaei Halimehjani ◽  
Petr Beier ◽  
Maryam Khalili Foumeshi ◽  
Ali Alaei ◽  
Blanka Klepetářová
Keyword(s):  
Amino Acids ◽  
Carbon Disulfide ◽  
Multicomponent Reaction ◽  
Michael Addition ◽  
Addition Reaction ◽  
Primary Amines ◽  
Oxidation Reactions ◽  
Michael Addition Reaction ◽  
Synthetic Utility ◽  
Reaction Proceeds

AbstractThiazolidine-2-thiones were prepared via a novel multicomponent reaction of primary amines (amino acids), carbon disulfide, and γ-bromocrotonates. The reaction proceeds via a domino alkylation/intramolecular Michael addition to provide the corresponding thiazolidine-2-thiones in high to excellent yields. By using diamines in this protocol, bis(thiazolidine-2-thiones) derivatives were synthesized. The synthetic utility of the adducts was demonstrated by hydrolysis, amidation, and oxidation reactions.

scholarly journals Michael Addition of Imidazole to α, β -Unsaturated Carbonyl/Cyano Compound

2018 ◽  
Vol 5 (1) ◽  
pp. 18-31
Author(s):  
Seetaram Mohapatra ◽  
Nilofar Baral ◽  
Nilima Priyadarsini Mishra ◽  
Pravati Panda ◽  
Sabita Nayak
Keyword(s):  
Organic Chemistry ◽  
Amino Acids ◽  
Anticancer Agents ◽  
Michael Addition ◽  
Addition Reaction ◽  
Bond Formation ◽  
Conjugate Addition ◽  
Michael Addition Reaction ◽  
Cyano Compounds ◽  
Nitrogen Bond

Introduction: Aza-Michael addition is an important reaction for carbon-nitrogen bond formation in synthetic organic chemistry. Expalantion: Conjugate addition of imidazole to α,β-unsaturated carbonyl/cyano compounds provides significant numbers of the biologically and synthetically interesting products, such as β-amino acids and β-lactams, which have attracted great attention for their use as key intermediates of anticancer agents, antibiotics and other drugs. Conclusion: This review addresses most significant method for the synthesis of N-substituted imidazole derivatives following Michael addition reaction of imidazole to α,β-unsaturated carbonyl/cyano compounds using ionic liquid/base/acid/enzyme as catalysts from year 2007-2017.

scholarly journals A Flavone Fluorescent Probe for Cysteine Detection

2019 ◽  
Vol 31 (12) ◽  
pp. 2909-2914
Author(s):  
Saleh N. Al-Busafi ◽  
Salma M. Al-Kindi ◽  
Fakhr Eldin O. Suliman ◽  
Aliya A. Al-Kalbani
Keyword(s):  
Amino Acids ◽  
Fluorescent Probe ◽  
1H Nmr ◽  
Michael Addition ◽  
Addition Reaction ◽  
Fluorescence Emission ◽  
Selective Detection ◽  
Michael Addition Reaction ◽  
Uv Visible ◽  
The Michael Addition

A new blue-emitting fluorescent probe 1 based on flavone structure was prepared for the selective detection of cysteine. The probe was prepared through three synthetic steps from commercially available starting materials. Selective detection of cysteine by probe 1 in the presence of other non-thiol amino acids was established by UV-visible and fluorescent experiments. A remarkable fluorescence emission was observed at 469 nm when cysteine was mixed with probe 1. The Michael addition reaction of cysteine to probe-1 was confirmed by 1H NMR technique.

Copper(I)-Promoted Michael-Addition Reaction of Organozincs of Esters, Nitriles, and ?-Amino Acids

1989 ◽  
Vol 28 (3) ◽  
pp. 351-353 ◽  
Author(s):  
Yoshinao Tamaru ◽  
Hiroto Tanigawa ◽  
Tetsuji Yamamoto ◽  
Zen-ichi Yoshida
Keyword(s):  
Amino Acids ◽  
Michael Addition ◽  
Addition Reaction ◽  
Michael Addition Reaction
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