Biocatalytic one-pot three-component synthesis of 3,3′-disubstituted oxindoles and spirooxindole pyrans using α-amylase from hog pancreas

被引：45
作者：
He, Tao [1 ]
Zeng, Qing-Qing [1 ]
Yang, Da-Cheng [1 ]
He, Yan-Hong [1 ]
Guan, Zhi [1 ]
机构：
[1] Southwest Univ, Sch Chem & Chem Engn, Key Lab Appl Chem Chongqing Municipal, Chongqing 400715, Peoples R China
来源：
RSC ADVANCES | 2015年 / 5卷 / 47期
基金：
中国国家自然科学基金;
关键词：
CATALYZED MICHAEL ADDITION; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE CONSTRUCTION; ENZYME PROMISCUITY; ALKALINE PROTEASE; NATURAL-PRODUCTS; LIPASE; CARBOHYDRATE; PROTEINASE; CONCISE;
D O I：
10.1039/c4ra16825a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
alpha-Amylase from hog pancreas displayed catalytic promiscuity in three-component reaction for the synthesis of 3,3'-disubstituted oxindoles and spirooxindole pyrans. The reactions between isatins, malononitrile and active methyl or active methylene compounds (acetone, nitromethane, indole, acetylacetone, 4-hydroxylcoumarin and dimedone) offered corresponding products via Knoevenagel/Michael reactions or Knoevenagel/Michael/cyclization reactions in one pot with high to excellent yields of up to 98% under mild reaction conditions. The alpha-amylase showed a broad spectrum of adaptability to various substrates. A possible mechanism of the alpha-amylase catalyzed three-component reaction was proposed.
引用
收藏
页码：37843 / 37852
页数：10
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