SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 4, 2008, Pages 529-534

Carbohydrates to functionalized pyridines: A new synthetic approach via enol-driven ring transformations

(4) Yadav, Lal Dhar Singh a Rai, Ankita a Rai, Vijai Kumar a Awasthi, Chhama a

a UNIVERSITY OF ALLAHABAD (India)

Author keywords

1,3 oxazin 2 ones; Carbohydrates; Microwaves; Mineral catalyzed; Pyridines; Solvent free

Indexed keywords

1,3 OXAZINE DERIVATIVE; ALCOHOL DERIVATIVE; ALKYL GROUP; CARBOHYDRATE; KETONE DERIVATIVE; LACTONE DERIVATIVE; PYRIDINE DERIVATIVE; PYRIDONE DERIVATIVE; SOLVENT; THIOL DERIVATIVE;

ARTICLE; CATALYSIS; DECARBOXYLATION; DRUG SYNTHESIS; MICHAEL ADDITION; MICROWAVE IRRADIATION;

EID: 40949126591 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1042760 Document Type: Article

Times cited : (9)

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16
- 40949112860
- General Procedure for the Synthesis of 6-Polyhydroxy-alkyl-1,3-oxazin- 2-ones 3 Thoroughly mixed aldose semicarbazone 11 (2.0 mmol) and Montmorillonite K-10 clay (0.20 g) were taken in a 20 mL vial and subjected to MW irradiation in a CEM Discover Focused Microwave Synthesis System at 90 °C for 10 min. After completion of the reaction as indicated by TLC, H 2O (10 mL) was added to give the crude product, which was recrystallized from EtOH to obtain an analytically pure sample of 3 as a white solid. Characterization Data for Synthesized Compounds Compound 3a: white solid; mp 145-148 °C IR(KBr, 3392, 3386, 3011, 1692 cm-1. 1H NMR (400 MHz, DMSO-d6, δ= 4.11 (dd, J2′Ha,2′Hb, 10.1 Hz, J1′H,2′Ha, 5.4 Hz, 1 H, 2′Ha, 4.30 dd, J1′H,2′Ha, 5-4 Hz, J 1′,2′Hb
- 5: C, 44.92; H, 4.85; N, 7.48. Found: C, 44.69; H, 4.73; N, 7.73.

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18
- 40949119090
- General Procedure for the Synthesis of 4-Polyhydroxyalkyl-1H- pyridin-2-ones 7, 8, and 2-Aryl-4-polyhydroxyalkylpyridines 9 An intimate solvent-free mixture of 1,3-oxazin-2-one 3 (2.4 mmol) and 1,3-oxathiolan-5-one 4 (2.4 mmol, or 1,3-oxazol-5-one 5 (2.4 mmol, or ketone 6 (2.4 mmol) in the presence of Montmorillonite K-10 clay (0.25 g) was taken in a 20 mL vial and subjected to MW irradiation in a CEM Discover Focused Microwave Synthesis System at 90 °C for 7-11 min. After completion of the reaction as indicated by TLC, H2O (10 mL) was added to give the crude product, which was recrystallized from EtOH to obtain an analytically pure sample of 7, 8, or 9 as a white solid. Characterization Data for Representative Compounds Compound 7a: white solid; mp 178-180 °C. IR (KBr, 3388-3361, 3015, 2550, 1692 cm -1. 1H NMR 400 MHz, DMSO-d6, δ, 1.57
- 2: C, 72.54; H, 6.09; N, 6.51. Found: C, 72.25; H, 6.27; N, 6.69.

19
- 40949093655
- General Procedure for the Synthesis of 3-Amino-4-polyhydroxyalkyl-1H- pyridin-2-ones 10 Compound 8 (2.0 mmol) was refluxed in H2SO4-H2O (15 mL, 4:3, v/v) for 45 min in an oil bath. The reaction mixture was cooled, and the desired product 10 was precipitated by adding concentrated NH4OH (specific gravity 0.88) under ice cooling and recrystallized from EtOH to obtain an analytically pure sample of 10. Characterization Data for Synthesized Compounds Compound 10a: white solid; mp 141-143°C IR (KBr, 3391-3367, 3015, 1692 cm-1. 1H NMR (400 MHz, DMSO-d6, δ, 3.77 (dd, J2′Ha,2′Hb, 10.3 Hz, J 1′H,2′Ha, 5.5 Hz, 1 H, 2′Ha, 4.13 (dd, J2′Ha,2′Hb, 10.3 Hz, J 1′H, 2′Hb, 2.8 Hz, 1 H, 2′Hb, 4.35 dd
- 4: C, 48.00; H, 6.04; N, 13.99. Found: C, 48.21; H, 5.89; N, 14.16.

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