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Synlett

Volumn , Issue 6, 2007, Pages 881-884

General, mild and efficient synthesis of β-enaminones catalyzed by ceric ammonium nitrate

(3) Sridharan, Vellaisamy a Avendaño, Carmen a Menendez J C a

a UNIVERSIDAD COMPLUTENSE DE MADRID (Spain)

Author keywords

dicarbonyl compounds; Ceric ammonium nitrate; Enaminones; Lanthanides; Lewis acids

Indexed keywords

AMINE; AMMONIUM NITRATE; BETA ENAMINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ROOM TEMPERATURE; SYNTHESIS;

EID: 34247101798 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-973862 Document Type: Article

Times cited : (58)

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- General Experimental Procedure for β-Enaminone Synthesis To a stirred solution of 3 mmol of amine 1 and 3 mmol of β-dicarbonyl compound 2 in 3 mL of EtOH was added 5 mol% of CAN. The mixture was stirred at r.t. for the time periods specified in Tables 1 and 2. After completion of the reaction the mixture was dissolved in CH2Cl 2, washed with H2O, dried, and evaporated. Analytically pure compounds 3 were obtained by a rapid column chromatography on Et3N-pretreated silica gel, eluting with PE-EtOAc mixtures. Characterization data for two representative, previously unknown enamines follow. Ethyl 2-(4-methylphenylamino)cyclohex-1-enecarboxylate (3b, viscous liquid. IR (neat, 3228.5, 2935.4, 2858.6, 1650.6, 1603.4, 1515.9, 1236.9, 1175.8, 1077.8 cm-1. 1H NMR (250 MHz, CDCl 3, δ 1.33 (t, J, 7.1 Hz, 3 H, 1.61-1.63 (m, 4 H, 2.26-2.40 (m, 7 H, 4.21 q
- 23NOS: C, 62.83; H, 10.11; N, 6.11; S, 13.98. Found: C, 62.76; H, 9.96; N, 5.86; S, 13.74.

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