Microwave-Assisted Synthesis of Substituted 2-(Benzylthio)imidazo[1,2<i>a</i>]pyrimidin-5-ones

Soh, Chai Hoon; Lam, Yulin

doi:10.1021/cc900176x

Cited by 9 publications

(21 citation statements)

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“…Soh et al described the synthesis of 2-(benzylthio)imidazo-[1,2-a]pyrimidin-5(1H)-ones on bromomethyl resin 118. 83 β-Keto ester 117 was reacted with thiourea to afford 5,6disubstituted-2-mercaptopyrimidin-4-one intermediate, which immediately react with resin 118 under microwave irradiation conditions provided resin bound pyrimidines 119. The resin 119 on reaction with bromoacetonitrile resulted in resin 120, which on subsequent self-cyclization with benzyl thiol followed by cleavage from the solid support yielded 2-(benzylthio)imidazo[1,2-a] pyrimidin-5(1H)-ones 121 (Scheme 28).…”

Section: Acs Combinatorial Sciencementioning

confidence: 94%

“…Soh et al described the synthesis of 2-(benzylthio)imidazo[1,2- a ]pyrimidin-5(1 H )-ones on bromomethyl resin 118 . β-Keto ester 117 was reacted with thiourea to afford 5,6-disubstituted-2-mercaptopyrimidin-4-one intermediate, which immediately react with resin 118 under microwave irradiation conditions provided resin bound pyrimidines 119 .…”

Section: Solid-phase Synthesis Of Imidazopyrimidinesmentioning

confidence: 99%

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Advances in the Solid-Phase Synthesis of Pyrimidine Derivatives

Aparna

Devaky

2019

ACS Comb. Sci.

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This Review describes the existing synthetic approaches for the solid-phase synthesis (SPS) of differently substituted and fused pyrimidine derivatives. These synthetic strategies are classified on the basis of the different synthetic routes leading to the particular type of pyrimidine heterocycle formed. The Review discusses the application of a variety of polystyrene derived supports for the construction of pyrimidine rings. The effect of microwave heating on the solid-phase synthesis is also addressed in the review.

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Section: Acs Combinatorial Sciencementioning

confidence: 94%

Section: Solid-phase Synthesis Of Imidazopyrimidinesmentioning

confidence: 99%

Advances in the Solid-Phase Synthesis of Pyrimidine Derivatives

Aparna

Devaky

2019

ACS Comb. Sci.

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“…Mw-assisted synthesis provided fast access to substituted 2-(benzylthio)imidazo[1,2- a ]pyrimidin-5(1 H )-ones . β-Keto ester 650 (Scheme ) was reacted with thiourea 651 to provide 5,6-disubstituted 2-mercaptopyrimidin-4-ones 652 , which were immobilized onto bromomethyl resin in a one-pot reaction.…”

Section: Cyclative Cleavagementioning

confidence: 99%

Traceless Solid-Phase Organic Synthesis

2019

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Traceless solid-phase synthesis represents an ultimate sophisticated synthetic strategy on insoluble supports. Compounds synthesized on solid supports can be released without a trace of the linker that was used to tether the intermediates during the synthesis. Thus, the target products are composed only of the components (atoms, functional groups) inherent to the target core structure. A wide variety of synthetic strategies have been developed to prepare products in a traceless manner, and this review is dedicated to all aspects of traceless solid-phase organic synthesis. Importantly, the synthesis does not need to be carried out on a linker designed for traceless synthesis; most of the synthetic approaches described herein were developed using standard, commercially available linkers (originally devised for solid-phase peptide synthesis). The type of structure prepared in a traceless fashion is not restricted. The individual synthetic approaches are divided into eight sections, each devoted to a different methodology for traceless synthesis. Each section consists of a brief outline of the synthetic strategy followed by a description of individual reported syntheses.

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“…However, alkylation of tetrahydropyrimidine/di-hydropyrimidine rings using PTC conditions generated S-monoalkylated (2nd position-alkylated derivatives) and/or simultaneous S-and N-dialkylated products (2nd and 3rd position-alkylated derivatives) [29]. Additionally, an attempt of selective N-alkylation (3rd position) of an S-benzylated intermediate yielded both N-and O-dialkylated products (3rd and 4th positions), simultaneously [30]. Furthermore, it has been reported that treatment of methylthiodihydropyrimidines/ methylthiotetrahydropyrimidines with hydrogen sulfide (H 2 S) afforded the corresponding thiouracil derivatives with selective substitution at the 3rd position, i.e., thiooxotetrahydroprimidinones [25].…”

Section: Introductionmentioning

confidence: 99%