期刊
SYNLETT
卷 -, 期 18, 页码 2763-2768出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0028-1083549
关键词
isatin; allylindium; Morita-Baylis-Hillman adduct; lactonisation; spirolactone oxindoles
资金
- DST (New Delhi) [SR/S1/OC-38/2005]
- CSIR (New Delhi)
A short and efficient synthesis of alpha-methylene-gamma-butyrolactone-3-spirooxindolones by the reaction of isomerised bromo derivatives of Morita-Baylis-Hillman adducts of isatin and formalehyde followed by acid-catalysed lactonisation has been achieved. The oxindolidino allyl bromide has been used for the first time for the allylation of aldehydes to afford a 2-oxindolidino homoallylic alcohol which on acid-catalysed lactonisation delivered the title compounds in excellent yield. Synthetic transformation of the spirolactone oxindole is demonstrated with the preparation of an oxirane derivative and a second Morita-Baylis-Hillman adduct.
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