New multicomponent domino reactions (MDRs) in water: Highly chemo-, regio- and stereoselective synthesis of spiro([1,3]dioxanopyridine)-4,6-diones and pyrazolo[3,4-b]pyridines

Ning Ma, Bo Jiang, Ge Zhang, Shu Jiang Tu, Walter Wever, Guigen Li

Research output: Contribution to journalArticlepeer-review

139 Scopus citations

Abstract

New multicomponent domino reactions (MDRs) have been established for the synthesis of spiro(pyrazolo[1,3]dioxanopyridine)-4,6-diones, spiro(isoxazolo[1,3]dioxanopyridine)-4,6-diones and pyrazolo[3,4-b]pyridines. The MDRs were conducted by reacting readily available and inexpensive starting materials in aqueous solution under microwave irradiation. A total of 26 examples were examined, and showed a broad substrate scope and high overall yields (76–93%). A new mechanism has been proposed to explain the reaction process and the resulting chemo-, regio- and stereoselectivity. The present green synthesis shows attractive characteristics such as the use of water as the reaction medium, one-pot conditions, short reaction periods (9–13 min), easy work-up/purification and reduced waste production without the use of any acids or metal promoters.

Original languageEnglish
Pages (from-to)1357-1361
Number of pages5
JournalGreen Chemistry
Volume12
Issue number8
DOIs
StatePublished - Aug 3 2010

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