Synthesis of a 2-benzocymantrenylpyridine and further mechanistic insights

Djukic, Jean‐Pierre; Iali, Wissam; Hijazi, Akram; Ricard, Louis

doi:10.1016/j.jorganchem.2010.11.012

Cited by 9 publications

(3 citation statements)

References 53 publications

(47 reference statements)

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“…1-(3-Methylpyridin-2-yl)-3-phenylpropan-2-one (5). Using general method A, 3 methyl-2-pyridinecarbonitrile (0.236 g, 2.0 mmol) gives compound 5 (0.391g, 1.74 mmol, 87%), isolated as a clear, yellow oil, R f = 0.30 (4:1 hexane:ether).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…2-(1H-Inden-3-yl)pyridine compounds (1) were examined by Merck researchers for use as growth hormone release promoters, 2 whereas compound 2 ( fenistil) is a well-known antihistamine drug. 3 Pyridylsubstituted indenes have also been used to prepare zirconium (3), 4 manganese (4), 5 and ruthenium complexes. 6 Cyclodehydration is a well-known route to carbocyclic products.…”

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confidence: 99%

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Cyclodehydrations Leading to Indene Products Having N-Heterocyclic Substituents

Boblak

Klumpp

2014

J. Org. Chem.

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In this Note, we describe superacid-promoted cyclodehydrations leading to functionalized indenes. The product indenes are synthesized having N-heterocyclic substituents, including pyridyl, imidazolyl, pyrimdyl, and other groups. A mechanism is proposed involving dicationic, superelectrophilic intermediates. The protonated N-heterocyclic rings are shown to dramatically lower the LUMO energy level of the carboxonium electrophile (compared to that of a similar uncharged system).

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Section: ■ Experimental Sectionmentioning

confidence: 99%

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confidence: 99%

Cyclodehydrations Leading to Indene Products Having N-Heterocyclic Substituents

Boblak

Klumpp

2014

J. Org. Chem.

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“…Indene derivatives exhibit a wide range of biological properties . In addition, they act as ligands to form different metallocene complexes, which have been extensively utilized as catalysts in the olefin polymerization process . Because of the importance of the indene moiety, different methods have been established to construct the indene core.…”

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confidence: 99%

In Situ Formed Acetal-Facilitated Synthesis of Substituted Indene Derivatives from o-Alkenylbenzaldehydes

Manojveer

Balamurugan

2015

Org. Lett.

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A new protocol has been developed for the synthesis of indene derivatives in a diastereoselective manner from o-alkenylbenzaldehydes and enolizable ketones in the presence of trimethyl orthoformate and catalytic triflic acid. This method involves tandem in situ formed acetal-assisted Claisen-Schmidt condensation followed by 5-exo-trig cyclization/Michael addition in one-pot. It has also been shown that the chalcones derived from o-alkenylbenzaldehydes and ketones can effectively be transformed into indene derivatives in the presence of TfOH catalyst alone.

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