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Synlett

Volumn , Issue 14, 2009, Pages 2249-2252

A mild protocol for the efficient synthesis of 5,6-unsubstituted 1,4-dihydropyridines

(2) Maiti, Swarupananda a Menéndez, J Carlos a

a UNIVERSIDAD COMPLUTENSE DE MADRID (Spain)

Author keywords

Cerium(IV); Dihydropyridines; Eliminations; Heterocycles; Lewis acids

Indexed keywords

1,4 DIHYDROPYRIDINE DERIVATIVE; 6 ALKOXY 2 METHYL 1,4,5,6 TETRAHYDROPYRIDINE DERIVATIVE; 6 ETHOXY 1,4,5,6 TETRAHYDROPYRIDINE; DIHYDROPYRIDINE DERIVATIVE; ETHYL 1 BUTYL 2 METHYL 1,4 DIHYDROPYRIDINE 3 CARBOXYLATE; ETHYL 1 BUTYL 2 METHYL 4 PHENYL 1,4 DIHYDROPYRIDINE 3 CARBOXYLATE; ETHYL 1 BUTYL 2,4 DIMETHYL 1,4 DIHYDROPYRIDINE 3 CARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 69249142311 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0029-1217719 Document Type: Article

Times cited : (23)

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- General experimental procedure: To a solution of a suitable primary amine (1.1 mmol) and β-keto ester (1 mmol) in anhydrous MeCN (5 mL) was added CAN (5 mol, The solution was stirred at room temperature for 30 minutes. To this solution was added a suitable α,β-unsaturated aldehyde (1.1 mmol) in EtOH (3 mmol, The reaction mixture was stirred at room temperature for 1 h, diluted with CH2Cl2 (15 mL) and washed with water (3 x 5 mL, The organic layer was dried over anhydrous Na2SO 4 and concentrated to dryness. The crude residue was dissolved in MeCN (10 mL) and neutral, grade I activity Al2O3 (5 g) was added. The suspension was heated under reflux for the time specified in Table 2. After completion of the reaction (verified by NMR, the mixture was diluted with CH2Cl2 and filtered through a layer of Celite, which was thoroughly washed with boiling CH2Cl2 50 mL
- 2 (299.4): C, 76.22; H, 8.42; N, 4.68. Found: C, 75.98; H, 8.31; N, 4.23.

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