Decades of synthesis and application of spiro cyclopropanes

The reaction of symmetrical (thio)barbituric acids with aldehydes in the presence of 4-methyl morpholine yielded a new form of 4-methyl morpholinium bis-(thio)barbiturate containing charge-separated intermolecular and eightmembered intramolecular H-bonds. X-ray Crystallography, FT-IR, and 1 H and 13 C-NMR spectroscopy techniques were used for structure characterizations. Some of these compounds showed potent anticancer activities. Cytotoxicity of the synthetic compounds against HeLa and MCF-7 cell lines were performed by MTT assay. In addition, a comparative molecular field analysis was carried out, and the effects of substituents on the biological activities of these compounds were explained.

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“…[ 15 ] One‐pot reaction of (thio)barbituric acids with aldehydes and cyanogen bromide yield spiro furo[2,3‐ d ] pyrimidines. [ 16–21 ]…”

Section: Introductionmentioning

confidence: 99%

4‐Methyl morpholinium bis‐(thio)barbiturates: Synthesis, structure, anticancer evaluation, and CoMFA study

Pesyan

Rashidnejad

Esmaeili

et al. 2020

J Chinese Chemical Soc

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The organocatalytic role of L-(+)-tartaric acid in the synthesis of 5-aryl-1,1′- and 5-aryl-3,1′-dimethyl-1H,1′H-spiro[furo[2,3-d]pyrimidine-6,5′-pyrimidine]2,2′,4,4′,6′(3H,3′H,5H)-pentaones

2020

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P(NMe₂)₃-Mediated Umpolung Spirocyclopropanation Reaction of p-Quinone Methides: Diastereoselective Synthesis of Spirocyclopropane-Cyclohexadienones

et al. 2020

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An unprecedented umpolung spirocyclopropanation reaction of p-quinone methides and α-keto carbonyls is described. Our umpolung strategy based on 1,6-conjugate addition and intramolecular nucleophilic substitution offers a new method for effective access to a series of highly functionalized spirocyclohexadienonyl cyclopropanes having two vicinal quaternary carbons in ≤98% yield and >20:1 dr. Significantly, cyclic and acyclic topological structures of α-keto carbonyls as 1,1-dipole one-carbon synthons have a distinct influence on the stereochemistry of products, showing a reversal of diastereoselectivity in this P(NMe2)3-mediated umpolung spirocyclopropanation.

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Decades of synthesis and application of spiro cyclopropanes

Cited by 5 publications

References 421 publications

4‐Methyl morpholinium bis‐(thio)barbiturates: Synthesis, structure, anticancer evaluation, and CoMFA study

4‐Methyl morpholinium bis‐(thio)barbiturates: Synthesis, structure, anticancer evaluation, and CoMFA study

The organocatalytic role of L-(+)-tartaric acid in the synthesis of 5-aryl-1,1′- and 5-aryl-3,1′-dimethyl-1H,1′H-spiro[furo[2,3-d]pyrimidine-6,5′-pyrimidine]2,2′,4,4′,6′(3H,3′H,5H)-pentaones

P(NMe₂)₃-Mediated Umpolung Spirocyclopropanation Reaction of p-Quinone Methides: Diastereoselective Synthesis of Spirocyclopropane-Cyclohexadienones

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Decades of synthesis and application of spiro cyclopropanes

Cited by 5 publications

References 421 publications

4‐Methyl morpholinium bis‐(thio)barbiturates: Synthesis, structure, anticancer evaluation, and CoMFA study

4‐Methyl morpholinium bis‐(thio)barbiturates: Synthesis, structure, anticancer evaluation, and CoMFA study

The organocatalytic role of L-(+)-tartaric acid in the synthesis of 5-aryl-1,1′- and 5-aryl-3,1′-dimethyl-1H,1′H-spiro[furo[2,3-d]pyrimidine-6,5′-pyrimidine]2,2′,4,4′,6′(3H,3′H,5H)-pentaones

P(NMe2)3-Mediated Umpolung Spirocyclopropanation Reaction of p-Quinone Methides: Diastereoselective Synthesis of Spirocyclopropane-Cyclohexadienones

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P(NMe₂)₃-Mediated Umpolung Spirocyclopropanation Reaction of p-Quinone Methides: Diastereoselective Synthesis of Spirocyclopropane-Cyclohexadienones