A facile synthesis of ferrocene grafted N-methyl-spiropyrrolidines through 1,3-dipolar cycloaddition of azomethine ylides

Tetrahedron Letters

Volumn 50, Issue 23, 2009, Pages 2818-2821

  Sureshbabu, A R ^a   Raghunathan, R ^a   Satiskumar, B K ^b  

^a UNIVERSITY OF MADRAS   (India)

^b PRESIDENCY COLLEGE   (India)

Author keywords

Azomethine ylide; Cycloaddition; Ferrocene; Spiroheterocycles; Spiropyrrolidines

Indexed keywords

AMPHOLYTE; AZOMETHINE YLIDE; FERROCENE; NINHYDRIN; PYRROLIDINE DERIVATIVE; SARCOSINE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 64549148819     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.175     Document Type: Article

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36. Representative procedure for the synthesis of spiropyrrolidines derivatives 4a: Method A: A solution of the ferrocene-derived dipolarophile 1a (1 mmol), ninhydrin 2 (1 mmol), and sarcosine 3 (1 mmol) was refluxed in 10 mL acetonitrile until the completion of the reaction as evidenced by TLC. The solvent was removed under reduced pressure and the crude product was subjected to column chromatography using petroleum ether: ethyl acetate (4:1) as eluent. The product 4a was then recrystallized from methanol.Method B: A solution of the ferrocene-derived dipolarophile 1a (1 mmol), ninhydrin 2 (1 mmol), and sarcosine 3 (1 mmol) was refluxed in 10 mL toluene using a Dean-stark apparatus. After the completion of the reaction as evidenced by TLC, the solvent was removed under reduced pressure and the crude product was subjected to column chromatography using petroleum ether:ethyl acetate (4:1) as eluent. The product 4a was then recrystallized from methanol.
37. 2: C, 67.35; H, 3.66; N, 2.31. Found: C, 67.19; H, 3.80; N, 2.47.
38. 4, unit cell parameters: a 10.2621 (6), b 10.9085, c 20.9435 (12), β 100.2100 (10), space group P21/n. Data acquisition: The Cambridge Crystallographic Data Center;deposit@ccdc.cam.ac.uk, http://www.ccdc.cam.ac.uk/deposit.