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Lithiation of N-protected-dihydro-1,4-benzoxaziness

✍ Scribed by Yansong J. Lu; Bin Hu; Mahavir Prashad; Shaum Kabadi; Oljan Repič; Thomas J. Blacklock

Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
77 KB
Volume
43
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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Lithiation of N‐protected‐2,3‐dihydro‐1,4‐benzoxazines is described. Lithiation of N‐(tert‐butoxycarbonyl)‐2,3‐dihydro‐1,4‐benzoxazine (1) with BuLi/TMEDA occurred in the α‐position to nitrogen on the heterocyclic ring, leading to the unexpected ring‐opened product 3. On the other hand, lithiation of N‐methyl‐2,3‐dihydro‐1,4‐benzoxazine (4) took place at the oxygen‐adjacent ortho‐position of the aromatic ring.

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