Expedient stereoselective synthesis of trifluoromethylated pyranonaphthoquinones

Dang Thi Tuyet Anh, Hoang Thi Phuong, Vu Ngoc Doan, Pham The Chinh, Nguyen Thanh Ha, Nguyen Thi Thu Ha, Nguyen Hung Huy, Ngo Quoc Anh, Nguyen Van Tuyen
Author affiliations

Authors

  • Dang Thi Tuyet Anh
  • Hoang Thi Phuong
  • Vu Ngoc Doan
  • Pham The Chinh
  • Nguyen Thanh Ha
  • Nguyen Thi Thu Ha
  • Nguyen Hung Huy
  • Ngo Quoc Anh
  • Nguyen Van Tuyen

DOI:

https://doi.org/10.15625/7619

Keywords:

Hydroxypyranonaphthoquinone, ammonium acetate

Abstract

Stereodefined and biologically relevant CF3-containing hydroxypyranonaphthoquinone carboxylates were prepared for the first time by a one-pot four-component condensation between 2-hydroxy-1,4-naphthoquinone, an aldehyde, ethyl 4,4,4-trifluoroacetoacetate and ammonium acetate. This transformation is presumed to proceed via aldol condensation/Mannich reaction followed by Michael addition and regio- and stereoselective 6-exo-trig cyclization, deamination and addition of water.

Keywords. Hydroxypyranonaphthoquinone, ammonium acetate.

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Published

01-12-2015

How to Cite

Tuyet Anh, D. T., Phuong, H. T., Doan, V. N., Chinh, P. T., Ha, N. T., Thu Ha, N. T., … Tuyen, N. V. (2015). Expedient stereoselective synthesis of trifluoromethylated pyranonaphthoquinones. Vietnam Journal of Chemistry, 53(5), 595. https://doi.org/10.15625/7619

Issue

Vol. 53 No. 5 (2015)

Section

Articles