Display options
Cite
Babu KR, Han W, Chen JB, et al. A three-component reaction of phosphorus ylides with isocyanates: facile synthesis of 2-amino-3-carboxylate-4-quinolones. Chem Commun (Camb). 2020;56(44):5909-5912doi: 10.1039/d0cc01401j.
Babu, K. R., Han, W., Chen, J. B., Li, Y., Tang, Y., Zhang, W., Xu, W., & Xu, S. (2020). A three-component reaction of phosphorus ylides with isocyanates: facile synthesis of 2-amino-3-carboxylate-4-quinolones. Chemical communications (Cambridge, England), 56(44), 5909-5912. https://doi.org/10.1039/d0cc01401j
Babu, Kaki Raveendra, et al. "A three-component reaction of phosphorus ylides with isocyanates: facile synthesis of 2-amino-3-carboxylate-4-quinolones." Chemical communications (Cambridge, England) vol. 56,44 (2020): 5909-5912. doi: https://doi.org/10.1039/d0cc01401j
Babu KR, Han W, Chen JB, Li Y, Tang Y, Zhang W, Xu W, Xu S. A three-component reaction of phosphorus ylides with isocyanates: facile synthesis of 2-amino-3-carboxylate-4-quinolones. Chem Commun (Camb). 2020 Jun 02;56(44):5909-5912. doi: 10.1039/d0cc01401j. PMID: 32342091.
Copy Download .nbib Format: NLM
Share it on

Chem Commun (Camb). 2020 Jun 02;56(44):5909-5912. doi: 10.1039/d0cc01401j.

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

Chemical communications (Cambridge, England)

Kaki Raveendra Babu, Wendan Han, Jian-Bo Chen, Yang Li, Yuhai Tang, Wenquan Zhang, Wenbo Xu, Silong Xu

Affiliations

  1. Department of Chemistry, School of Science, and Xi'an Key Laboratory of Sustainable Energy Materials Chemistry, Xi'an Jiaotong University, Xi'an 710049, P. R. China. [email protected].
  2. Institute of Chemical Materials, China Academy of Engineering Physics (CAEP), Mianyang 621900, P. R. China.
  3. College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014, P. R. China. [email protected].

PMID: 32342091 DOI: 10.1039/d0cc01401j

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.

Publication Types