Sequential change in one-pot, three-component protocol: A stepping stone in heterocyclic synthesis

Raja, R.; Dinesh, Murugan; Archana, Sivasubramaniyan; George, Jaabil; Sakthivel, P.; Ponnuswamy, Alagusundaram; Jayakumar, Mohan Raj; Murugavel, S.

doi:10.1080/00397911.2016.1178775

Cited by 14 publications

(8 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1). [42][43][44] Appalanaidu et al applied carbon disulfide in the microwave assisted preparation of symmetrical thioureas in the one-pot synthesis of 2-iminothiazolines (Scheme 1, eq. 2).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Convenient Multicomponent One‐Pot Synthesis of 2‐Iminothiazolines and 2‐Aminothiazoles Using Elemental Sulfur Under Aqueous Conditions

et al. 2021

View full text Add to dashboard Cite

Dedicated to professor Ferenc Fülöp on the occasion of his 70th birthday.Herein, we present a novel one-pot aqueous reaction for the synthesis of 2-iminothiazolines and 2-aminothiazoles using isocyanides, amines, sulfur, and 2'-bromoacetophenones. The three-component preparation of thioureas is followed by the one-pot cyclization leading to the heterocyclic product. This efficient and mild procedure features excellent step-and atomeconomy and enables the chromatography-free preparation of diversely substituted 2-iminothiazoline and 2-aminothiazole derivatives.

show abstract

Section: Introductionmentioning

confidence: 99%

“…reported the preparation of 2‐iminothiazolines in one‐pot, based on the in situ generation of thioureas from amines and isothiocyanates followed by the ring annulation with 2’‐bromoacetophenones (Scheme 1, eq. 1) [42–44] . Appalanaidu et al .…”

Section: Introductionmentioning

confidence: 99%

Convenient Multicomponent One‐Pot Synthesis of 2‐Iminothiazolines and 2‐Aminothiazoles Using Elemental Sulfur Under Aqueous Conditions

et al. 2021

View full text Add to dashboard Cite

show abstract

“…The traditional approach to the synthesis of imidazole‐2‐thiones is based on the interaction of α‐aminoketones and isothiocyanates. [ 33–35 ] In this case, the starting α‐aminoketones can be preliminarily obtained or generated in situ by the reaction of α‐hydroxyketones [ 36 ] or α‐haloketones [ 37 ] with various amines. It is important to note that generally α‐aminoketones have low stability.…”

Section: Resultsmentioning

confidence: 99%

Multicomponent one‐pot synthesis of novel imidazole‐2‐thione derivatives containing allomaltol fragment

Komogortsev

Melekhina

Lichitsky

et al. 2021

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

A convenient method for the synthesis of novel imidazole‐2‐thione derivatives containing allomaltol fragment was elaborated. This approach includes one‐pot multicomponent reaction of allomaltol, arylglyoxals, primary amines followed by addition of alkyl or aryl isothiocyanates. It was shown that the key intermediates of the studied process are substituted α‐aminoketones and the corresponding imidazolidine‐2‐thione. The advantages of this synthesis are mild reaction conditions, atom economy, and easy workup procedure, which can avoid chromatographic purifications. The structures of an intermediate imidazolidine‐2‐thione and one of the final imidazole‐2‐thiones were determined by X‐ray diffraction.

show abstract

“…Total chemocontrol was observed since the formation of regioisomer 5′ { 1 , 1 , 1 } was also possible due to the unsymmetrical thiourea 3 { 1 , 1 }. Moreover, N , N -annulated product 6 { 1 , 1 , 1 } was not detected due to the sequential addition of reactants used in the same reaction …”

Section: Resultsmentioning

confidence: 99%

Base Controlled Three-Component Regioselective Synthesis of 2-Imino Thiazolines and 2-Thioxoimidazolin-4-ones

et al. 2019

View full text Add to dashboard Cite

Base-controlled regioselective synthesis of 2imino thiazolines and 2-thioxoimidazolin-4-ones was achieved to use a one-pot reaction between chiral amino esters, isothiocyanates, and α-bromoketones/alkyl halides. This three-component coupling reaction in acetonitrile provides 2-imino thiazolines, whereas the formation of 2-thioxoimidazolin-4-ones was observed under basic conditions at ambient temperature. The corresponding products were obtained in good to excellent yield with broad substrate scope. Isolation of thiourea and thiohydantoin intermediates disclosed the course of the reaction mechanism.

show abstract

Sequential change in one-pot, three-component protocol: A stepping stone in heterocyclic synthesis

Cited by 14 publications

References 26 publications

Convenient Multicomponent One‐Pot Synthesis of 2‐Iminothiazolines and 2‐Aminothiazoles Using Elemental Sulfur Under Aqueous Conditions

Convenient Multicomponent One‐Pot Synthesis of 2‐Iminothiazolines and 2‐Aminothiazoles Using Elemental Sulfur Under Aqueous Conditions

Multicomponent one‐pot synthesis of novel imidazole‐2‐thione derivatives containing allomaltol fragment

Base Controlled Three-Component Regioselective Synthesis of 2-Imino Thiazolines and 2-Thioxoimidazolin-4-ones

Contact Info

Product

Resources

About