Directed ortho-metalation (DoM) strategy has been applied for the development of a short procedure for the regiospecific synthesis of [phenyl-2 H 4 ]-2-bromo-benzylamine 6 starting from commercially available [phenyl-2 H 5 ]-benzoyl chloride 1. A strong isotope effect was observed during the ortho-s
Synthesis of benzoxazole-[phenyl-13C6] by directed ortho-metalation chemistry
✍ Scribed by Volker Derdau
- Publisher
- John Wiley and Sons
- Year
- 2004
- Tongue
- French
- Weight
- 97 KB
- Volume
- 47
- Category
- Article
- ISSN
- 0022-2135
- DOI
- 10.1002/jlcr.792
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✦ Synopsis
Abstract
A new method for the preparation of benzoxazole‐[phenyl‐^13^C~6~] (1) starting from aniline‐[^13^C~6~] (4) has been developed involving directed ortho‐metalation (D__o__M) chemistry. The synthesis comprises four steps and an overall yield of 39% was obtained. Copyright © 2003 John Wiley & Sons, Ltd.
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## Abstract A procedure for the synthesis of benzo[__e__][1,3]thiazine‐2,4‐diones from benzamides by directed lithiation and sequential treatment with sulfur and phosgene is reported. Use of thiophosgene afforded 2‐thioxo‐2,3‐dihydro‐benzo[__e__][1,3] thiazin‐4‐ones. Application of this methodology