An efficient synthesis of thiopyrano[5,6-c]coumarin/[6,5-c]chromones through intramolecular domino Knoevenagel hetero Diels-Alder reactions

Tetrahedron Letters

Volumn 47, Issue 13, 2006, Pages 2265-2270

  Jayashankaran, Jayadevan ^a   Manian, Rathna Durga R S ^a   Raghunathan, Raghavachary ^a  

^a UNIVERSITY OF MADRAS   (India)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYCOUMARIN; ALDEHYDE; CHROMONE DERIVATIVE; COUMARIN DERIVATIVE; THIOPYRANO[5,6 C]COUMARIN; UNCLASSIFIED DRUG;

ARTICLE; DIELS ALDER REACTION; DRUG SYNTHESIS; KNOEVENAGEL CONDENSATION; MICROWAVE IRRADIATION; PRENYLATION; SOLID;

BETULACEAE;

EID: 33344474176     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.01.083     Document Type: Article

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34. Representative procedure for the preparation of thiopyrano-pyrano ring systems: Method A: To a refluxing solution of unsymmetrical 1,3-dione (1 mmol) in 10 mL of dry ethanol, aldehyde 2 or 5 (1 mmol) was added and the reaction mixture was refluxed until the disappearance of the starting material as evidenced by thin layer chromatography. After completion of the reaction, the solvent was evaporated and the residue was subjected to flash column chromatography using hexane/ethyl acetate mixture (9:1). Method B: A solution of unsymmetrical 1,3-dione (1 mmol) and the corresponding aldehyde (1 mmol) in dry ethanol/toluene were irradiated using a domestic microwave oven (Kenstar, 800 W power) until the thin layer chromatography indicated complete disappearance of the starting material. After the removal of the solvent, the crude reaction mixture was subjected to flash column chromatography as above. Method C: A mixture of 1,3-dione (1 mmol), the corresponding aldehyde (1 mmol) and K-10 Montmorillonite clay (1.0 g) was thoroughly ground in a mortar. The reaction mixture was irradiated using a domestic microwave oven (Kenstar, 800 W power) until the complete disappearance of the starting material as evidenced by thin layer chromatography. After completion of the reaction, the clay was separated by filtration and extracted with dichloromethane (2 × 15 mL). Removal of the solvent and purification of the crude reaction mixture by flash column chromatography gave the pure product.
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36. 3S: C, 72.50; H, 5.00; N, 5.83. Found: C, 72.33; H, 4.81; N, 6.08.