Addition-cyclization reactions of ethyl isothiocyanatoacetate with carboxylic acid hydrazides

1987 ◽  
Vol 52 (1) ◽  
pp. 113-119 ◽  
Author(s):  
Miroslav Veverka ◽  
Miroslav Marchalín
Keyword(s):  
Carboxylic Acid ◽  
Sodium Ethoxide ◽  
Cyclization Reaction ◽  
Thermal Cyclization ◽  
Cyclization Reactions ◽  
Effect Of Substituents

Ethyl (3-substituted 5-thioxo-1,2,4-triazolin-4-yl)acetates were prepared by addition-cyclization reaction of ethyl isothiocyanatoacetate with carboxylic acid hydrazides in the presence of sodium ethoxide. Thermal cyclization of the adduct in dimethylformamide afforded 1-acetamido-2-thiohydantoin. The effect of substituents on the cyclization course and the thione-thiol tautomerism are discussed.

Catalytic enantioselective cascade Michael/cyclization reaction of 3-isothiocyanato oxindoles with exocyclic α,β-unsaturated ketones en route to 3,2′-pyrrolidinyl bispirooxindoles

2016 ◽  
Vol 14 (43) ◽  
pp. 10175-10179 ◽  
Author(s):  
Satavisha Kayal ◽  
Santanu Mukherjee
Keyword(s):  
Cyclization Reaction ◽  
Cyclization Reactions ◽  
Unsaturated Ketones ◽  
Tertiary Amino

Cascade Michael/cyclization reactions between 3-isothiocyanato oxindoles and exocyclic α,β-unsaturated ketones are shown to proceed in the presence of a tertiary amino-squaramide catalyst and furnish 3,2′-pyrrolidinyl bispirooxindoles with excellent enantioselectivities (up to 99 : 1 er).

Triamide macrocyclic chloride receptors via a one-pot tandem reduction–condensation–cyclization reaction

2017 ◽  
Vol 15 (23) ◽  
pp. 4937-4940 ◽  
Author(s):  
Harekrushna Behera ◽  
Venkatachalam Ramkumar ◽  
Nandita Madhavan
Keyword(s):  
Cyclization Reaction ◽  
Chloride Binding ◽  
Cyclization Reactions ◽  
One Pot

A chloride binding triamide macrocycle has been developed in one pot from the corresponding monomer via tandem reduction–condensation–cyclization reactions.

scholarly journals Thiol-to-amine cyclization reaction enables screening of large libraries of macrocyclic compounds and the generation of sub-kilodalton ligands

2019 ◽  
Vol 5 (8) ◽  
pp. eaaw2851 ◽  
Author(s):  
S. S. Kale ◽  
M. Bergeron-Brlek ◽  
Y. Wu ◽  
M. G. Kumar ◽  
M. V. Pham ◽  
...  
Keyword(s):  
Drug Development ◽  
Structure Analysis ◽  
Drug Targets ◽  
Macrocyclic Ligands ◽  
Cyclization Reaction ◽  
Thrombin Inhibitor ◽  
Macrocyclic Compounds ◽  
Cyclization Reactions ◽  
X Ray ◽  
High Yields

Macrocyclic compounds are an attractive modality for drug development, but the limited availability of large, structurally diverse macrocyclic libraries hampers the discovery of leads. Here, we describe the discovery of efficient macrocyclization reactions based on thiol-to-amine ligations using bis-electrophiles, their application to synthesize and screen large libraries of macrocyclic compounds, and the identification of potent small macrocyclic ligands. The thiol-to-amine cyclization reactions showed unexpectedly high yields for a wide substrate range, which obviated product purification and enabled the generation and screening of an 8988 macrocycle library with a comparatively small effort. X-ray structure analysis of an identified thrombin inhibitor (Ki = 42 ± 5 nM) revealed a snug fit with the target, validating the strategy of screening large libraries with a high skeletal diversity. The approach provides a route for screening large sub-kilodalton macrocyclic libraries and may be applied to many challenging drug targets.

Facile synthesis of 2,3-benzodiazepines using one-pot two-step phosphate-assisted acylation–hydrazine cyclization reactions

2018 ◽  
Vol 16 (21) ◽  
pp. 4013-4020 ◽  
Author(s):  
Akinari Sumita ◽  
Jinhee Lee ◽  
Yuko Otani ◽  
Tomohiko Ohwada
Keyword(s):  
Cyclization Reaction ◽  
Cyclization Reactions ◽  
Acylation Reaction ◽  
Facile Synthesis ◽  
One Pot

We present a one-pot two-step methodology, in which an unprotected amino is tolerated, for rapidly synthesizing 2,3-benzodiazepines via phosphate-assisted acylation reaction and hydrazine cyclization reaction.

Iodine-mediated regioselective 5-endo-dig electrophilic cyclization reaction of selenoenynes: synthesis of selenophene derivatives

2017 ◽  
Vol 4 (2) ◽  
pp. 277-282 ◽  
Author(s):  
Renan P. Pistoia ◽  
Juliano A. Roehrs ◽  
Davi F. Back ◽  
Gilson Zeni
Keyword(s):  
Cyclization Reaction ◽  
Electrophilic Cyclization ◽  
Cyclization Reactions

Selenoenynes underwent electrophilic cyclization reactions with iodine in the presence of an appropriate nucleophile to give 3-iodo-selenophenes and 3-organoselenyl-selenophenes.

ChemInform Abstract: Synthesis and Thermal Cyclization Reactions of Methyl Isocrotonate Derivatives.

ChemInform ◽  
1987 ◽  
Vol 18 (34) ◽  
Author(s):  
N. KAWAHARA ◽  
T. SHIMAMORI ◽  
T. ITOH ◽  
H. TAKAYANAGI ◽  
H. OGURA
Keyword(s):  
Thermal Cyclization ◽  
Cyclization Reactions

scholarly journals The use of 3-bromopropionic acid for the determination of protein thiol groups

1973 ◽  
Vol 131 (4) ◽  
pp. 637-642 ◽  
Author(s):  
A. F. Bradbury ◽  
D. G. Smyth
Keyword(s):  
Carboxylic Acid ◽  
Intramolecular Cyclization ◽  
Iodoacetic Acid ◽  
Cyclization Reaction ◽  
Thiol Groups ◽  
Protein Thiol

S-Carboxymethylcysteine, formed by the reaction of iodoacetic acid with cysteine, was found to undergo intramolecular cyclization to yield 3-oxo-(2H,3H,5H,6H-1,4-thiazine)-5-carboxylic acid. The cyclization was studied under various conditions and the product was isolated and characterized. S-Carboxyethylcysteine, formed by the reaction of 3-bromopropionic acid with cysteine, did not undergo the cyclization reaction. The use of 3-bromopropionic acid was examined as an alternative to iodoacetic acid for the protection and determination of protein thiol groups.

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