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DOI: 10.1055/s-0040-1719832
A Facile Synthesis of 2-Aminobenzoxazines Based on IodineCatalyzed Desulfurative Cyclization
This work was financially supported by the Japan Society for the Promotion of Science (JSPS) KAKENHI (Grant No. 17K07776).
Abstract
A facile and environmentally benign access to N-aryl/alkyl-4H-benzoxazin-2-amines is achieved from 1-[2-(hydroxymethyl)phenyl/alkyl]-3-phenylthioureas under transition-metal-free conditions. The conversions occur smoothly in the presence of a catalytic amount of molecular iodine and hydrogen peroxide as the oxidant in tetrahydrofuran at room temperature to afford moderate to good yields (28–90%) of the desired products within 2 hours. This method reports the first examples of the catalytic transformations of 1-[2-(hydroxymethyl)phenyl/alkyl]-3-phenylthioureas into N-aryl/alkyl-4H-benzoxazin-2-amines based on desulfurative cyclization.
Key words
molecular iodine - desulfurative cyclization - benzoxazines - one-pot synthesis - Suzuki–Miyaura cross-couplingSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1719832.
- Supporting Information
Publication History
Received: 30 May 2021
Accepted after revision: 16 August 2021
Article published online:
05 October 2021
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Related studies including I2/TBHP-mediated oxidative coupling of 2-aminobenzyl alcohols with isocyanides and cyclization of ureas derived from anthranilic acids and isocyanates using a polymer-supported carbodiimide have also been reported, see:
For recent advances on iodine-mediated organic synthesis, see: