A greener approach for the synthesis of 1-N-methyl-(spiro[2.3′]oxindolespiro[3.2″]/spiro[2.3′]indan-1,3-dionespiro[2.2″])cyclopentanone-4-aryl pyrrolidines

Tetrahedron Letters

Volumn 48, Issue 2, 2007, Pages 319-322

  Sridhar, Gowri ^a,b   Gunasundari, T ^b   Raghunathan, R ^b  

^a STELLA MARIS COLLEGE   (India)

^b UNIVERSITY OF MADRAS   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AZOMETHINE YLIDE; CARBAMIC ACID DERIVATIVE; CYCLOPENTANONE DERIVATIVE; N,N DIMETHYLAMMONIUM N',N' DIMETHYLCARBAMATE; PYRROLIDINE DERIVATIVE;

ARTICLE; CYCLOADDITION; DECARBOXYLATION; METHODOLOGY; MICROWAVE RADIATION; SYNTHESIS;

EID: 33845193435     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.11.002     Document Type: Article

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21. 4 and extracted with ethyl acetate. The solvent was removed in vacuum and the product was purified through column chromatography using petroleum ether ethyl acetate mixture (9:1). General procedure for the solvent-free microwave promoted cycloaddition reactions of the azomethine ylide generated from isatin 6, sarcosine 7 with 2-arylidene-1-cyclopentanones 3a-d and 5e. A mixture of isatin 6 (1 mmol), sarcosine 7 (1 mmol), 2-monoarylidene cyclopentanones 3a-d, 5e (1 mmol) and 1 g of Bentonite clay was thoroughly mixed in a boiling tube which was loosely closed and immersed in a silica gel bath in a beaker and irradiated in microwave oven for about 10 min at the maximum microwave power level (600 W) for two 5 min durations with intermittent cooling. The temperature during irradiation rose to a maximum of about 158 °C as determined by measuring the maximum temperature of the silica gel bath immediately after irradiation was over by gently stirring the silica gel with the thermometer. After the completion, the reaction mixture was cooled and added to water (5 mL) and extracted with diethyl ether (5 mL). After filtering, the etheral layer was washed with water and dried with anhydrous sodium sulfate. The solvent was then removed under vacuum. The crude product was chromatographed on silica gel using hexane-ethyl acetate (5:1) as eluant to give 8a-d and 9e.
22. 3: C, 76.67; H, 6.67; N, 7.78. Found: C, 76.49; H, 6.59; N, 7.67.
23. Govind M.M., Selvanayagam S., Velmurugan D., Ravikumar K., Sridhar G., and Raghunathan R. Acta Cryst. E59 (2003) o1438-o1440
24. 3: C, 76.88; H, 5.85; N, 3.90. Found: C, 76.99; H, 5.98; N, 4.05.