標題: Microwave-Assisted Tandem Transformation on an Ionic-Liquid Support: Efficient Synthesis of Pyrrolo/Pyridobenzimidazolones and Isoindolinone-Fused Benzimidazoles
作者: Thummanagoti, Suman
Yellol, Gorakh S.
Sun, Chung-Ming
應用化學系
Department of Applied Chemistry
關鍵字: heterocycles;ionic liquids;microwave chemistry;supported synthesis;tandem reactions
公開日期: 5-九月-2011
摘要: A tandem transformation that involves the formation of three bonds and two heterocyclic rings in a one-pot fashion through amino-alkylation of an ionic-liquid-immobilized diamine with keto acids followed by successive double intramolecular cyclizations to afford a tricyclic framework has been explored. This tandem cyclization has been utilized to develop a rapid and efficient method to synthesize various pyrrolo[1,2-a]benzimidazolones and pyrido[1,2-a]benzimidazolones on an ionic-liquid support by using focused microwave irradiation. The application of this tandem cyclization was further extended to the aromatic keto acids to provide isoindolinone-fused benzimidazoles, a structurally heterogeneous library with skeletal diversity. The outcome of the cascade reaction was confirmed by the X-ray crystallographic study of the product directly attached to the ionic-liquid support. Use of the ionic liquid as a soluble support facilitates purification by simple precipitation along with advantages like high loading capacity, homogeneous reaction conditions, and monitoring of the reaction progress by regular conventional spectroscopic methods, whereas application of microwave irradiation greatly accelerates the rate of the reactions.
URI: http://dx.doi.org/10.1002/asia.201100277
http://hdl.handle.net/11536/19304
ISSN: 1861-4728
DOI: 10.1002/asia.201100277
期刊: CHEMISTRY-AN ASIAN JOURNAL
Volume: 6
Issue: 9
起始頁: 2471
結束頁: 2480
顯示於類別:期刊論文


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