4.8 Article

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

期刊

GREEN CHEMISTRY
卷 12, 期 8, 页码 1357-1361

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/c0gc00073f

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资金

  1. Jiangsu Education Committee [08QLT001]
  2. Graduate Foundation of Jiangsu Province [CX09S_043Z]
  3. Graduate Foundation of Xuzhou Normal University [09YLA005]
  4. Xuzhou Normal University [09XKXK01]
  5. Natural Science Foundation [09KJB150011]
  6. Robert A Welch Foundation [D-1361]
  7. NIH [R03DA026960]

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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.

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