A novel entry to dispiropyrrolo-bicyclo[2.2.1]heptanes through sequential 1,3-dipolar and Diels-Alder cycloaddition reactions

Tetrahedron Letters

Volumn 47, Issue 5, 2006, Pages 829-832

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

^a UNIVERSITY OF MADRAS   (India)

Author keywords

[No Author keywords available]

Indexed keywords

HEPTANE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLOADDITION; DIELS ALDER REACTION; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; X RAY DIFFRACTION;

BETULACEAE;

EID: 29544451139     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.11.089     Document Type: Article

References (32)

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29. Representative procedure for the preparation of dispiropyrrolidine cycloadducts: A solution of sarcosine (1 mmol), acenaphthaquinone/ninhydrin/ isatin (1 mmol), and 3-furfurylidene-4-chromanone/2-furfurylidene-1-tetralone (1 mmol) were refluxed in aqueous methanol. Completion of the reaction was evidenced by TLC analysis. The solvent was then removed in vacuo and the crude subjected to column chromatography using petroleum ether-ethyl acetate as eluent.
30. 4: C, 72.00; H, 5.00; N, 7.00. Found: C, 72.29; H, 5.18; N, 6.85.
31. Representative procedure for the preparation of spiropyrrolo-bicyclo[2.2. 1]heptane cycloadducts: A solution of dispiroheterocycle (1 mmol) obtained in the previous step was refluxed in toluene with dimethylacetylene dicarboxylate (1.2 mmol) under a nitrogen atmosphere until the completion of the reaction as evidenced by TLC analysis. The solvent was then removed in vacuo. The crude was then subjected to column chromatography using petroleum ether-ethyl acetate as eluent.
32. +).