1-(p-Chlorophenyl)-1,2,3,4,5,6-hexahydro-2,5-benzodiazocine

Kim, Donghan; Santilli, Arthur A.; Sulkowski, Theodore S.; Childress, Scott J.

doi:10.1021/jo01286a113

Cited by 9 publications

(3 citation statements)

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“…However, improved procedures to access 1a and 1b are available. 14,15 The reactivity of these bifunctional systems towards amines was therefore investigated.…”

Section: Resultsmentioning

confidence: 99%

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2-Substituted-Isoindoles: A Novel Synthetic Route and a Study of the Diels–Alder and Michael Reactions

Voitenko

Sypchenko

Levkov

et al. 2011

Journal of Chemical Research

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A novel one-step procedure for the synthesis of 2-substituted-isoindoles and 1-aryl-2-substituted-isoindoles is described. The procedure is based on the reaction of 2-(bromomethyl)benzaldehyde or 2-(bromomethyl)benzophen-one derivatives with primary aromatic or aliphatic amines. Reactions of 1,2-diarylisoindoles with N-phenylmaleimide were studied. Refluxing the reactants in i-PrOH in the presence of triethylamine leads to the formation of Diels–Alder endo-adducts; whilst refluxing in AcOH in the presence of AcONa affords Michael adducts. The structure of the latter was confirmed by X-ray diffraction.

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“…However, improved procedures to access 1a and 1b are available. 14,15 The reactivity of these bifunctional systems towards amines was therefore investigated.…”

Section: Resultsmentioning

confidence: 99%

“…Melting points were determined on a Boetius apparatus and are uncorrected. Elemental analyses were carried out with a Vario MICRO Cube elemental analyser.2-(Bromomethyl)benzaldehyde 1a 14 and 2-(bromomethyl) phenyl](4-chlorophenyl)methanone 1b 15 were prepared as described previously in the literature.…”

Section: Methodsmentioning

confidence: 99%

2-Substituted-Isoindoles: A Novel Synthetic Route and a Study of the Diels–Alder and Michael Reactions

Voitenko

Sypchenko

Levkov

et al. 2011

Journal of Chemical Research

View full text Add to dashboard Cite

show abstract

“…The [2-(bromomethyl)phenyl] (4-chlorophenyl)methanone (1a), which is commonly available, was chosen as a model to study the reaction with 2aminopyridines. 8…”

mentioning

confidence: 99%