A three-component reaction of phosphorus ylides with isocyanates: facile synthesis of 2-amino-3-carboxylate-4-quinolones

被引:13
作者
Babu, Kaki Raveendra [1 ,2 ]
Han, Wendan [1 ,2 ]
Chen, Jian-Bo [3 ]
Li, Yang [1 ,2 ]
Tang, Yuhai [1 ,2 ]
Zhang, Wenquan [3 ]
Xu, Wenbo [4 ]
Xu, Silong [1 ,2 ]
机构
[1] Xi An Jiao Tong Univ, Sch Sci, Dept Chem, Xian 710049, Peoples R China
[2] Xi An Jiao Tong Univ, Xian Key Lab Sustainable Energy Mat Chem, Xian 710049, Peoples R China
[3] China Acad Engn Phys, Inst Chem Mat, Mianyang 621900, Sichuan, Peoples R China
[4] Shandong Normal Univ, Coll Chem Chem Engn & Mat Sci, Jinan 250014, Peoples R China
基金
中国国家自然科学基金;
关键词
ALLYLIC ALKYLATION; 4-QUINOLONES; ROUTE; ACIDS; OLEFINATION; CYCLIZATION; ALLYLATION; INHIBITORS; CARBONATES; ANILINES;
D O I
10.1039/d0cc01401j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A three-component reaction between one molecule of phosphorus ylides (P-ylides) and two molecules of isocyanates for the rapid assembly of 2-amino-3-carboxylate-4-quinolones is described. The mechanism may involve the addition of a P-ylide to an isocyanate followed by 1,3-H shift to form a carbamoyl stabilized P-ylide. The intermediate then reacts with another aryl isocyanate via Wittig/ketenimine-ketene rearrangement/6 pi-electrocyclization/1,3-H shift to finally afford the 4-quinolones.
引用
收藏
页码:5909 / 5912
页数:4
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