Synthesis of 4H-benzo[e][1,3]oxazin-4-ones by a carbonylation–cyclization domino reaction of ortho-halophenols and cyanamide

Åkerbladh, Linda and Chow, Shiao L. and Odell, Luke R. and Larhed, Mats (2017) Synthesis of 4H-benzo[e][1,3]oxazin-4-ones by a carbonylation–cyclization domino reaction of ortho-halophenols and cyanamide. ChemistryOpen, 6 (5). pp. 620-628. ISSN 2191-1363 (https://doi.org/10.1002/open.201700130)

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Abstract

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.

ORCID iDs

Åkerbladh, Linda, Chow, Shiao L. ORCID logoORCID: https://orcid.org/0000-0002-3600-0497, Odell, Luke R. and Larhed, Mats;
  • Item type:Article
    ID code:90385
    Dates:
    Date
    Event
    16 October 2017
    Published
    16 August 2017
    Published Online
    10 July 2017
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:27 Aug 2024 16:20
    Last modified:16 Oct 2024 11:17
    URI:https://strathprints.strath.ac.uk/id/eprint/90385
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