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Issue 8, 2010
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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

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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.

Graphical abstract: 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

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Article information


Submitted
03 May 2010
Accepted
09 Jun 2010
First published
24 Jun 2010

Green Chem., 2010,12, 1357-1361
Article type
Communication

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

N. Ma, B. Jiang, G. Zhang, S. Tu, W. Wever and G. Li, Green Chem., 2010, 12, 1357
DOI: 10.1039/C0GC00073F

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