A three-component reaction of phosphorus ylides with isocyanates: facile synthesis of 2-amino-3-carboxylate-4-quinolones. Issue 44 (28th April 2020)

• Record Type: Journal Article
• Authors: Babu, Kaki Raveendra; Han, Wendan; Chen, Jian-Bo; Li, Yang; Tang, Yuhai; Zhang, Wenquan; Xu, Wenbo; Xu, Silong
• Is Part Of: Chemical communications. Volume 56:Issue 44(2020)
• Page Start: 5909
• Page End: 5912
• Publication Date: 2020-04-28
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d0cc01401j
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : A three-component catalyst-free reaction between one molecule of phosphorus ylides and two molecules of isocyanates provides a facile synthesis of 2-amino-3-carboxylate-4-quinolones. Abstract : 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/6π-electrocyclization/1, 3-H shift to finally afford the 4-quinolones.