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7-bromoisatin was treated with excess PhMgBr to afford tertiary alcohol 9 in 96 % yield. Isatin oxime triflates undergo a facile fragmentation which is promoted by DBU, to form anthranilonitriles after hydrolytic work-up.
K. C. Nicolaou,; Marco Bella,; David Y.-K. Chen,; Xianhai Huang,; Taotao Ling,; Scott A. Snyder.Total Synthesis of Diazonamide A. Angew. Chem. Int. Ed. 2002, 41(18), pg no.
James B. Campbell Jr.,; Timothy V. Davenport. Synthesis of Anthranilonitriles by Fragmentation of Isatin Oxime Triflates. Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry. 1989, 19 (13-14), 2255-2263.
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P280a-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.