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Volumn , Issue 9, 2008, Pages 1357-1360

Reactions of heterocyclic ketene aminals with Baylis-Hillman acetates: A novel synthesis of tetrahydropyridine-fused 1,3-diazaheterocycles

Author keywords

Baylis Hillman acetates; Heterocyclic ketene aminals; Synthesis; Tetrahydropyridine fused 1,3 diazaheterocycles

Indexed keywords

ACETIC ACID; HETEROCYCLIC COMPOUND; KETENE DERIVATIVE;

ARTICLE; BAYLIS HILLMAN REACTION; CHEMICAL REACTION KINETICS; METHODOLOGY; STEREOSPECIFICITY;

EID: 45849089935 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1072788 Document Type: Article

Times cited : (58)

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24
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- General Method for the Synthesis of 5a, 6, and 7 Baylis-Hillman acetate 3 or 4 (0.47 mmol) and HKAs 1 or 2 (0.47 mmol) were stirred in CH2Cl2 (20 mL) at 0°C for 1 h and then stirred at r.t. for further 6 h. Solvents were evaporated in vacuo and the residue was passed through a short silica gel chromatographic column, eluting with EtOAc-PE (1:1) to afford the desired products 5a, 6, or 7. When the reaction was carried out in THF or DMF at r.t, as mentioned in the main text, compound 5b was isolated together with 5a. Compound 5a: light yellow solid; mp 194-195°C 1H NMR (300 MHz, CDCl3, δ, 2.03 (m, 2 H, 2.60 (dd, J, 16.08, 3.82 Hz, 1H, 3.05 (ddd, J, 16.11, 3.77, 1.91 Hz, 1 H, 3.25-3.37 (m, 4 H, 4.51 (m, 1 H, 5.06 (s, 1 H, 7.26-7.43 (m, 10 H, Ar, 12.48 (s, 1 H, NH, 13C NMR 75 MHz, CDCl3, δ, 20.88, 24.84, 37
- 3): δ = 2.88 (dd, J = 15.52, 3.79 Hz, 1 H), 3.22 (ddd, J = 15.51, 4.81, 1.02 Hz, 1 H), 3.49-3.82 (m, 4 H), 4.85 (dd, J = 6.34, 3.76 Hz, 1 H), 5.16 (d, J = 2.96 Hz, 1 H), 6.37-6.40 (m, 2 H, furan ring), 7.32 (s, 4 H, Ph)

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