A versatile synthetic route to 1,5-dithiocins from o-mercapto aromatic aldehydes

1999 ◽  
Vol 77 (1) ◽  
pp. 113-121 ◽  
Author(s):  
Ian WJ Still ◽  
Rosanne Natividad-Preyra ◽  
F Dean Toste
Keyword(s):  
Amino Acids ◽  
Primary Amine ◽  
Methyl Esters ◽  
Aromatic Aldehydes ◽  
Primary Amines ◽  
Synthetic Route ◽  
General Reaction ◽  
Limited Success ◽  
Facile Preparation ◽  
General Method

An earlier procedure for the facile preparation of benzo-fused 1,5-dithiocins 2a-2c from o-mercapto- benzaldehydes has been improved and shown to be capable of extension to the preparation of several naphthalene-derived analogues. The general method also afforded several N-alkylated 1,5-dithiocins 4, 5 by replacing NH3 with the appropriate primary amine. It was found that N-acylation of the 1,5-dithiocins was successful only with methyl chloroformate. Attempted N-phenylation met with limited success but was shown to be unnecessary since even the less reactive aniline readily undergoes the general reaction of primary amines. When simple α-amino acids, or their methyl esters, were employed as the primary amine in the reaction with o-mercaptobenzaldehyde, the formation of the N-alkylated 1,5-dithiocins 4a, 17a,17b with accompanying loss of -COOH or -COOMe was observed, in preparatively useful yields. A mechanism is proposed for this interesting transformation.Key words: 1,5-dithiocins, α-amino acids, N-acylation, decarboxylation.

scholarly journals Synthesis of Bis-2,3-dihydroquinazolin-4(1H)-ones and 2,3-Dihydroquinazolin-4(1H)-ones Derivatives with the Aid of Silica-Supported Preyssler Nanoparticles

2013 ◽  
Vol 2013 ◽  
pp. 1-14 ◽  
Author(s):  
Ali Gharib ◽  
Bibi Robabeh Hashemipour Khorasani ◽  
Manouchehr Jahangir ◽  
Mina Roshani ◽  
Reza Safaee
Keyword(s):  
Primary Amine ◽  
Ammonium Carbonate ◽  
Aromatic Aldehydes ◽  
Product Yield ◽  
Primary Amines ◽  
Isatoic Anhydride ◽  
One Pot ◽  
High Yields ◽  
First Time

One-pot three-component condensation of isatoic anhydride with primary amines or ammonium carbonate and aromatic aldehydes in refluxing ethanol in the presence of catalytic amounts of silica-supported preyssler nanoparticles (SPNP) afforded the corresponding 2,3-dihydroquinazolin-4(1H)-ones in high yields, and bis-dihydroquinazolinones were synthesized for the first time by a novel pseudo-five-component condensation of isatoic anhydride, a primary amine, and a dialdehyde in water. The catalyst is reusable and can be applied several times without any decrease in product yield.

scholarly journals A GENERAL REACTION OF AMINO ACIDS. II

1928 ◽  
Vol 78 (3) ◽  
pp. 745-756
Author(s):  
H.D. Dakin ◽  
Randolph West
Keyword(s):  
Amino Acids ◽  
General Reaction

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.

Synthesis of 2-Aryl-5-alkyl-fulleropyrrolidines: Metal-Free-Mediated Reaction of [60]Fullerene with Aromatic Aldehydes and Inactive Primary Amines

2017 ◽  
Vol 82 (16) ◽  
pp. 8617-8627 ◽  
Author(s):  
Meng Zhang ◽  
Hui-Juan Wang ◽  
Fa-Bao Li ◽  
Xin-Xin Zhong ◽  
Yong-Shun Huang ◽  
...  
Keyword(s):  
Aromatic Aldehydes ◽  
Primary Amines ◽  
Metal Free

Sodium borohydride: A versatile reagent in the reductive N-monoalkylation of α-amino acids and α-amino methyl esters

2002 ◽  
Vol 80 (7) ◽  
pp. 779-788 ◽  
Author(s):  
Giancarlo Verardo ◽  
Paola Geatti ◽  
Elena Pol ◽  
Angelo G Giumanini
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Sodium Borohydride ◽  
Carbonyl Compounds ◽  
Condensation Reaction ◽  
Methyl Esters ◽  
Reducing Agent ◽  
Reductive Condensation ◽  
Versatile Reagent

α-Amino acids and α-amino methyl esters are easily converted to their N-monoalkyl derivatives by a reductive condensation reaction using several carbonyl compounds in the presence of sodium borohydride. This reducing agent has shown a wide versatility with minor but essential procedural variations. The reaction allows the α-monodeuterium labeling of the new N-substituent by use of sodium borodeuteride.Key words: α-amino acid, α-amino methyl esters, sodium borohydride, reductive N-monoalkylation, carbonyl compounds.

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