A novel approach to functionalised 5,7,8,9-tetrahydropyrimido[4,5-b][1,4]diazepin-6-ones using intramolecular palladium-catalysed amidation

Carr, Gregory R.; Feron, J. Lyman; Johnson, Paul D.; Roberts, Craig; Rudge, David A.; Simpson, Iain; Wrigley, Gail L.

doi:10.1016/j.tetlet.2012.03.125

Cited by 4 publications

(1 citation statement)

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“…Further chemical transformations using the synthesized tetra-functionalized methane derivatives were performed. Adduct 5Da , derived from acrylamide 1D and propylamine 4a , has an electrophilic α,β-unsaturated carbonyl function and a nucleophilic amino group; thus, intramolecular Michael addition was conducted. The yield of 1,2,5,6-tetrahydropyrimidin-4(3 H )-one 12 was 62% when an ethanol solution of aminal 5Da was heated at 140 °C for 2 days in a sealed tube (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Bis(functionalized) Aminals via Successive Nucleophilic Amidation and Amination

et al. 2023

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The central carbonyl group of diethyl mesoxalate (DEMO) exhibits high electrophilicity that allows it to be attacked by versatile nucleophiles. Even a less nucleophilic acid amide serves as a nucleophile to produce N,O-acetal upon treatment with DEMO in the presence of acetic anhydride. When the obtained N,O-acetal was treated with a base, the elimination of acetic acid generated Nacylimine in situ. N-Acylimine is also highly electrophilic, allowing it to accept the second nucleophilic addition by an amine, resulting in α,α-bis(functionalized) aminals. This protocol facilitates the modification of the two different amino groups by altering nucleophiles, resulting in the production of tetra-functionalized methane derivatives on demand. The ring closure between the amide moiety and the amino group was achieved using the structural features to form a six-membered ring.

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Section: Resultsmentioning

confidence: 99%