The first example of an intramolecular Diels–Alder furan (IMDAF) reaction of iminium salts and its application in a short and simple synthesis of the isoindolo[1,2-a]isoquinoline core of the jamtine and hirsutine alkaloids

Zubkov, Fedor I.; Ershova, Julya D.; Zaytsev, Vladimir P.; Обушак, Н. Д.; Matiychuk, V. S.; Соколова, Е. А.; Khrustalev, Victor N.; Varlamov, A. V.

doi:10.1016/j.tetlet.2010.10.046

Cited by 28 publications

(7 citation statements)

References 13 publications

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“…No formation of alcohol 4b or ketone 5b was observed. It is worth noting that this N ‐crotylaniline cyclized considerably more slowly than the corresponding N ‐allylaniline studied under the same conditions previously,6 but N ‐allylfurylamines might be quite sensitive to steric effects in the dienophile part of the molecule 4b . N ‐Allylamines are normally believed to be stable under acidic conditions and show good tolerance of, for instance, acid‐mediated reduction of nitro groups,15 hydrolysis of amides,16 and deformylations,17 but loss of allylic moieties from N ‐allylnaphthylamines was reported as a side reaction when aza‐Claisen rearrangements at elevated temperatures were attempted 18.…”

Section: Resultsmentioning

confidence: 55%

Mechanistic Investigation of the Reaction of Epoxides with Heterocumulenes Catalysed by a Bimetallic Aluminium Salen Complex

Beattie¹,

North²

2014

Chemistry A European J

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The bimetallic aluminium(salen) complex [(Al(salen))2O] is known to catalyse the reaction between epoxides and heterocumulenes (carbon dioxide, carbon disulfide and isocyanates) leading to five-membered ring heterocycles. Despite their apparent similarities, these three reactions have very different mechanistic features, and a kinetic study of oxazolidinone synthesis combined with previous kinetic work on cyclic carbonate and cyclic dithiocarbonate synthesis showed that all three reactions follow different rate equations. An NMR study of [Al(salen)]2O and phenylisocyanate provided evidence for an interaction between them, consistent with the rate equation data. A variable-temperature kinetics study on all three reactions showed that cyclic carbonate synthesis had a lower enthalpy of activation and a more negative entropy of activation than the other two heterocycle syntheses. The kinetic study was extended to oxazolidinone synthesis catalysed by the monometallic complex Al(salen)Cl, and this reaction was found to have a much less negative entropy of activation than any reaction catalysed by [Al(salen)]2O, a result that can be explained by the partial dissociation of an oligomeric Al(salen)Cl complex. A mechanistic rationale for all of the results is presented in terms of [Al(salen)]2O being able to function as a Lewis acid and/or a Lewis base, depending upon the susceptibility of the heterocumulene to reaction with nucleophiles.

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Section: Resultsmentioning

confidence: 55%

Mechanistic Investigation of the Reaction of Epoxides with Heterocumulenes Catalysed by a Bimetallic Aluminium Salen Complex

Beattie¹,

North²

2014

Chemistry A European J

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“…Diazonium salts are important reagents in organic synthesis, which are easily obtained from readily available aromatic amines. The utilization of diazonium salts in the design and synthesis of combinatorial libraries of furane Gorak et al, 2009;Obushak et al, 2008), pyrazole (Matiichuk et al, 2008), and 1,2,3-triazole derivatives, as well as some fused heterocycles Zelisko et al, 2015;Chaban et al, 2017;Zubkov et al, 2010;Klenina et al, 2017;Chaban et al, 2018) has been shown in our previous works. In this work we developed the new method of the synthesis of N-[5-R-benzyl)-1,3-thiazol-2-yl]-4,5dihydro-1H-imidazole-2-carboxamide 3a-e based on diazonium salt as a started reagents.…”

Section: Chemistrymentioning

confidence: 67%

Synthesis and antitumor properties of some new N-(5-R-benzyl-1,3-thiazol-2-yl)-4,5-dihydro-1H-imidazole-2-carboxamides

et al. 2020

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New N-(5-R-benzyl-1,3-thiazol-2-yl)-2-morpholin-4-yl-2-oxoacetamides have been prepared in good yields via the reaction of N-(5-R-benzyl-1,3-thiazol-2-yl)-2-chloroacetamides with sulfur and morfoline. These compounds react with ethendiamine to form a series of novel N-[5-R-benzyl)-1,3-thiazol-2-yl]-4,5-dihydro-1H-imidazole-2-carboxamides with excellent yields. Anticancer activity screening of synthesized compounds was carried out within the framework of the Developmental Therapeutic Program of the National Cancer Institute's (DTP, NCI, Bethesda, Maryland, USA). It was shown that compounds are promising for new anticancer agents' search.

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“…Continuing our works (Zimenkovskii et al 2006;Matiichuk et al 2008;Obushak et al 2009;Pokhodylo et al 2009a, b;Zubkov et al 2010;Klenina et al 2013Klenina et al , 2017Chaban et al 2014Chaban et al , 2016Chaban et al , 2017aChaban et al , b, 2018aChaban et al , b, 2019aLozynska et al 2015;Zelisko et al 2015;Tymoshuk et al 2019), on the synthesis and study of biological activity of azole derivatives we prepare combinatorial libraries of [5-(1H-benzoimidazol-2-ylmethylene)-4-oxo-2-thioxo-thiazolidin-3-ylcarboxilc and investigated their anticancer activities. We have been developed the method of the synthesis of 1H-benzoimidazole-2-carbaldehyde (4).…”

Section: Chemistrymentioning

confidence: 98%

Synthesis and anticancer properties of 5-(1H-benzoimidazol-2-ylmethylene)-4-oxo-2-thioxothiazolidin-3-ylcarboxilic acids

Horishny¹,

Чабан²,

Matiychuk³

2021

PHAR

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The reaction of 1H-benzoimidazole-2-carbaldehyde with 4-oxo-2-thioxothiazolidin-3-ylcarboxilic acids was studied and the combinatorial library of 5-(1H-benzoimidazol-2-ylmethylene)-4-oxo-2-thioxothiazolidin-3-ylcarboxilic acids has been prepared. The structures of target compounds 8a-f, 9 and 10a, b were confirmed by using 1H NMR spectroscopy and elemental analysis. The synthesized compounds were selected by the National Cancer Institute (NCI) Developmental Therapeutic Program for the in vitro cell line screening to investigate their anticancer activity. The tested compounds displayed a weak to medium anticancer activity. The most sensitive cell lines turned out to be SNB-75 of CNS Cancer (GP = 74.84–85.73%) and UO-31, Renal cancer (GP = 71.53–82.16%) and to compound 10a K-562 Leukemia cell lines (GP = 57.14). Graphical abstract

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The first example of an intramolecular Diels–Alder furan (IMDAF) reaction of iminium salts and its application in a short and simple synthesis of the isoindolo[1,2-a]isoquinoline core of the jamtine and hirsutine alkaloids

Cited by 28 publications

References 13 publications

Mechanistic Investigation of the Reaction of Epoxides with Heterocumulenes Catalysed by a Bimetallic Aluminium Salen Complex

Mechanistic Investigation of the Reaction of Epoxides with Heterocumulenes Catalysed by a Bimetallic Aluminium Salen Complex

Synthesis and antitumor properties of some new N-(5-R-benzyl-1,3-thiazol-2-yl)-4,5-dihydro-1H-imidazole-2-carboxamides

Synthesis and anticancer properties of 5-(1H-benzoimidazol-2-ylmethylene)-4-oxo-2-thioxothiazolidin-3-ylcarboxilic acids

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