SCOPUS 정보 검색 플랫폼

Volumn , Issue 15, 2008, Pages 2348-2354

An efficient protocol for multicomponent stereoselective synthesis of 3-amino-2(1H)-pyridinones using CeCl3·7H2O/NaI as a reaction promoter

(2) Yadav, Lal Dhar S a Kapoor, Ritu a

a UNIVERSITY OF ALLAHABAD (India)

Author keywords

Chalcones; Heterocycles; Lewis acid; Multicomponent reaction; Stereoselective synthesis

Indexed keywords

2 PHENYL 1,3 OXAZOLON 5 ONE; 3 AMINO 2 (1H)PYRIDINONE DERIVATIVE; AMINE; CERIUM TRICHLORIDE; CHALCONE DERIVATIVE; CHLORIDE; KETONE DERIVATIVE; PYRIDONE DERIVATIVE; SODIUM IODIDE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL STRUCTURE; HYDROLYSIS; MICHAEL ADDITION; ONE POT SYNTHESIS; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 52949134831 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078272 Document Type: Article

Times cited : (15)

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- General Procedure for the Synthesis of 3-Benzamido-2 (1H)-pyridinones 5 A mixture of 1,3-oxazolon-5-one 1 (5 mmol, chalcone 2 (5 mmol, amine 3 (5 mmol, CeCl 3·7H2O (1 mmol, and NaI (1 mmol) in EtOH (25 mL) was stirred at r.t. for 3-5 h. After completion of the reaction, as indicated by TLC (hexane-EtOAc, 8:2, v/v, the solvent was evaporated under reduced pressure, the residue thus obtained extracted with Et2O (3 x 15 mL, The extract was evaporated to leave the crude product which was recrystallized from EtOH to afford a distereomeric mixture >96:<4; in the crude products the ratio was >94:6 as indicated by 1H NMR spectroscopy, The product on second recrystallization from EtOH furnished analytically pure pale yellow crystal of a single diastereomer 4, which was assigned the trans stereochemistry on the basis of 1H NMR spectra. Characterization Data for Rep
- 3: C, 78.46; H, 5.52; N, 5.90. Found: C, 78.81; H, 5.30; N, 5.56.

47
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- General Procedure for the Synthesis of 3-Amino-2 (1H, Pyridinone 4 Compound 5 (2.0 mmol) was refluxed in H 2SO4-H2O (15 mL, 4:3, v/v) for 30 min in an oil bath. The reaction mixture was cooled, filtered, and the desired product 4 was precipitated by adding concentrated NH4OH (d, 0.88) under ice cooling and recrystallized from EtOH to afford an analytically pure sample of 4 (Table 1, Characterization Data for Representative Compounds Compound 4 (Table 2, entry 1, pale yellow crystals; yield 90, mp 135-134°C. IR (KBr, 3342, 3011, 1699, 1608, 1540, 1430, 749, 703 cm-1. 1H NMR (400 MHz, DMSO-d6 and D2O-TMS, δ, 3.96 (d, 1 H, J, 9.9 Hz, 3-H, 4.15 (dd, 1 H, J, 9.9, 5.9 Hz, 4-H, 5.90 (d, 1 H, J, 5.9 Hz, 5-H, 7.19-7.90 (m, 15 Harom, 13C NMR100 MHz, DMSO-d6
- 2: C, 77.81; H, 5.99; N, 7.56. Found: C, 78.12; H, 6.29; N, 7.26.

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