Synthesis of amines of the di-and trifurylmethane series

Nevolina, Tatyana A.; Строганова, Т. А.; Shevlyakov, M. V.; Бутин, А. В.

doi:10.1007/s10593-007-0058-1

Chem Heterocycl Compd

2007

DOI: 10.1007/s10593-007-0058-1

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Synthesis of amines of the di-and trifurylmethane series

Tatyana A. Nevolina

Т. А. Строганова

M. V. Shevlyakov

et al.

Abstract: Methods are proposed for the synthesis of amines of the di-and trifurylmethane series -prospective compounds for the production of polymers and macrocyclic molecules -on the basis of 2-(2-furylmethyl)-1,3-isoindolinedione.

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Cited by 5 publications

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“…The synthesis of substrate 4 for the Mannich/Diels-Alder reaction was achieved by protection of furfurylamine 5, followed by formylation using phosphoryl chloride in DMF to give aldehyde 8, 19 which readily reacted with allylamine to afford the Schiff base 4 in high yield (Fig. 2).…”

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confidence: 99%

Tandem Mannich/Diels–Alder reactions for the synthesis of indole compound libraries

Petersen

et al. 2016

RSC Adv.

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mentioning

confidence: 99%

Tandem Mannich/Diels–Alder reactions for the synthesis of indole compound libraries

Petersen

et al. 2016

RSC Adv.

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Gold Catalysis: Catalyst Oxidation State Dependent Dichotomy in the Cyclization of Furan–Yne Systems with Aromatic Tethers

Hashmi

Hofmann

Shi

et al. 2012

Chemistry A European J

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Four different synthetic strategies led to a variety of furan-yne systems that contained an aryl system in the tether. Due to the short routes to these systems (four steps or less), a small library of substrates could easily be prepared. These were treated with AuCl(3) or with the Gagosz's catalyst Ph(3)PAuNTf(2) complex. The AuCl(3)-catalyzed reactions delivered highly substituted fluorene derivatives, a class of compounds of great importance as precursors for luminophores with extraordinary abilities. Conversely, a different mechanistic pathway was observed with the cationic gold(I) catalyst. In the latter case, a mechanistically interesting reaction cascade initiated a formal alkyne insertion into the furyl-sp(3)-C bond, which gave indene derivatives as the final products. This new reaction pathway depends on the aromatic moiety in the tether, which stabilizes a crucial cationic intermediate as a benzylic cation.

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