Traceless and Stereoselective Synthesis of Tetrahydro-β-carbolinethiohydantoins by Microwave Irradiation

Chang, Wong Jin; Kulkarni, Manohar V.; Sun, Chung‐Ming

doi:10.1021/cc050098j

Cited by 23 publications

(9 citation statements)

References 41 publications

(50 reference statements)

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“…The classical preparation of 2-thiohydantoins (2THs) is identical in concept to that of I2Ts; acylation of an a-amino ester or acid with a thiocyanate is followed by cyclization of the intermediate. [22][23][24][25][26][27][28] This reaction also traces back at least as far as Marckwald and co-workers. More recently it became famous as the basis of the Edman degradation, wherein the unmasked N-terminus of a peptide is acylated with a thiocyanate; cyclization at the resultant athioureido amide terminus expels a 2TH and a peptide shortened by one amino acid residue.…”

supporting

confidence: 67%

Facile Conversion of Amino Acids into 1-Alkyl Imidazole-2-thiones, and Their Oxidative Desulfurization to Imidazoles with Benzoyl Peroxide

Wolfe¹,

Schreiner²

2007

Synthesis

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Glycine was acylated with isothiocyanates and condensed to 3-alkyl 2-thiohydantoins, which were reduced with a mixture of sodium borohydride and lithium chloride and dehydrated to 1-alkyl imidazole-2-thiones. These were oxidatively desulfurized to imidazoles with benzoyl peroxide. No chromatography was required for model compounds. The methods developed were used to elaborate tyrosine to 1,4-di(p-methoxybenzyl)imidazole, a common intermediate in the syntheses of three imidazoles from the sponge Leucetta.

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supporting

confidence: 67%

Facile Conversion of Amino Acids into 1-Alkyl Imidazole-2-thiones, and Their Oxidative Desulfurization to Imidazoles with Benzoyl Peroxide

Wolfe¹,

Schreiner²

2007

Synthesis

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“…[11][12][13] In the past decades, great efforts have been devoted to introducing thiohydantoins and their derivatives into desirable substrates, such as pharmacophores and synthetic intermediates. [14][15][16][17] Compounds containing the thiohydantoin structural motif have been identified to display a wide range of biological activities. For example, many of them exhibit anticonvulsant, 18 anti-epileptic, 19 antimicrobial, 20 antiviral, 21 antineoplastic, 22 hypolipidemic, 23 antithrombotic, 24 and potential antitumor activities, 25,26 etc.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and cytotoxicity of palladium(II) complex of 3-[(2-hydroxy-benzylidene)-amino]-2-thioxo-imidazolidin-4-one

Šmit

Pavlovic

Radosavljevic-Mihailovic³

et al. 2013

JSCS

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The polydentate ligand, 3-[(2-hydroxy-benzylidene)-amino]-2-thioxo-imidazolidin-4-one, was synthesized by intermolecular cyclocondensation reaction of 2-hydroxybenzaldehyde thiosemicarbazone and ethylchloroacetate. Novel palladium(II) complex was obtained by nucleophilic substitution of both DMSO ligands from cis-[Pd(DMSO)2Cl2] with iminic nitrogen and thiolactamic sulfur from ligand. The structure of compounds was characterized on the basis of their spectral data. The cytotoxic activity of the ligand and palladium(II) complex was studied on tumor cell lines: human colon carcinoma HCT-116 and SW-480 cells using MTT viability test. The results show that investigated palladium(II) complex has significantly greater cytotoxic effect compared to ligand. [Projekat Ministarstva nauke Republike SRbije, br. 172011 and III41010

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“…Sun and Co‐workers also reported the polymer‐supported synthesis of thiohydantoin fused β‐carboline alkaloids under microwave irradiation (Scheme ) . The N ‐Boc protected L ‐tryptophan was immobilized on PEG to yield bis ‐ester 290 using DCC in the presence of DMAP.…”

Section: β‐Carboline Fused Heterocycles Synthesized Via Post‐pictet‐smentioning

confidence: 99%

Post‐Pictet‐Spengler Cyclization (PPSC): A Strategy to Synthesize Polycyclic β‐Carboline‐Derived Natural Products and Biologically Active N‐Heterocycles

Singh

Kumar

Patil³

et al. 2020

Adv Synth Catal

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Pictet-Spengler reaction is a typical condensation reaction of β-arylethylamine or Tryptamine with an aldehyde or ketone followed by ring closure to generate tetrahydroisoquinoline (THIQ) and Tetrahydro-β-carboline (THβC), respectively. Both these key skeletons represent huge range of structurally diverse naturally occurring isoquinoline and indole alkaloids. Nature has synthesized structurally complex Reserpine, Ajmalicine as well as other related alkaloids using various biosynthetic pathways via Pictet-Spengler reaction followed by post-Pictet-Spengler cyclization (PPSC) stratergy. This biosynthetic process is the short and reliable method to access diverse range of polycyclic heterocycles. Over the period of last sixty years, several researchers have synthesized complex alkaloids without highlighting the synthetic utility of the post-Pictet-Spengler cyclization strategy. We summarized the synthesis of numerous natural products and related natural product inspired heterocyclic scaffolds which follow the PPSC strategy to demonstrate its usefulness for the construction of diverse compound collection.

show abstract

Traceless and Stereoselective Synthesis of Tetrahydro-β-carbolinethiohydantoins by Microwave Irradiation

Cited by 23 publications

References 41 publications

Facile Conversion of Amino Acids into 1-Alkyl Imidazole-2-thiones, and Their Oxidative Desulfurization to Imidazoles with Benzoyl Peroxide

Facile Conversion of Amino Acids into 1-Alkyl Imidazole-2-thiones, and Their Oxidative Desulfurization to Imidazoles with Benzoyl Peroxide

Synthesis, characterization and cytotoxicity of palladium(II) complex of 3-[(2-hydroxy-benzylidene)-amino]-2-thioxo-imidazolidin-4-one

Post‐Pictet‐Spengler Cyclization (PPSC): A Strategy to Synthesize Polycyclic β‐Carboline‐Derived Natural Products and Biologically Active N‐Heterocycles

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