Synthesis of 4H-Benzo[e][1,3]oxazin-4-ones by a Carbonylation–Cyclization Domino Reaction of ortho-Halophenols and Cyanamide

Linda Åkerbladh, Shiao Y. Chow, Luke R. Odell*, Mats Larhed

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract / Description of output

A mild and convenient one-step preparation of 4H-1,3-benzoxazin-4-ones by a domino carbonylation–cyclization process is developed. Readily available ortho-iodophenols are subjected to palladium-catalyzed carbonylative coupling with Mo(CO)6 and cyanamide, followed by a spontaneous, intramolecular cyclization to afford 4H-1,3-benzoxazin-4-ones in moderate to excellent yields. Furthermore, the scope of the reaction is extended to include challenging ortho-bromophenols. Finally, to highlight the versatility of the developed method, Mo(CO)6 is successfully replaced with a wide array of CO-releasing reagents, such as oxalyl chloride, phenyl formate, 9-methylfluorene-9-carbonyl chloride, and formic acid, making this an appealing strategy for the synthesis of 4H-benzo[e][1,3]oxazin-4-ones.

Original languageEnglish
Pages (from-to)620-628
Number of pages9
JournalChemistryOpen
Volume6
Issue number5
Early online date16 Aug 2017
DOIs
Publication statusPublished - 1 Oct 2017

Keywords / Materials (for Non-textual outputs)

  • 4H-benzo[e][1,3]oxazin-4-ones
  • carbonylation
  • domino reactions
  • halophenols
  • heterocycles

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