Stereoselective synthesis of (E)-N,N-diethyl-3-(imidazo[1,2-a]pyrid-2-yl)-2-(phenylsulfonyl)propenamide

Add time:08/25/2019    Source:sciencedirect.com

The title compound, gem-amidovinylsulfone 3, was synthesized stereoselectively by aldolic condensation of N,N-diethylphenylsulfonylacetamide 1 on imidazo[1,2-a]pyridine-2-carbaldehyde 2 adding Et3N at the end. The X-ray crystal structure of 3 [C20H21N3O3S: Mr=383.5, monoclinic, P21, a=8.191(4) Å, b=21.132(2) Å, c=11.752(1) Å, β=96.40(2)°, V=2022(1) Å3, Z=4 (two molecules per asymmetric unit), Dcalc=1.260 g cm−3, λ(Mo Kα)=0.71073 Å, μ=0.184 mm−1, F(000)=808, T=293(2)K, R=0.059 for 5105 observed reflections with I≥2σ(I)] was determined, and confirmed the (E) configuration.

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