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2005
Amines
Q 0120
24- 079
Reactions of N- and C-Alkenylanilines. Part 6. Synthesis of 6-Methyl-2-[(E or
Z)-1-propenyl]anilines and the Corresponding Anilides and Their Reaction with
Bromine. — The addition of bromine to carbamates (V) and (VIII) is accompanied by
intramolecular cyclization with formation of a mixture of dibromides and benzoxazinones [cf. compounds (VI)/(VII) and (IX)/(X)]. The use of NBS instead of Br2 leads
only to ethoxybenzoxazines (XI) and (XII), while the reaction of N-mesyl derivative
(XIV) with bromine affords a mixture of stereoisomeric dibromides (XV) and (XVI).
— (AFON'KIN, I. S.; SOTNIKOV, A. M.; GATAULLIN, R. R.; SPIRIKHIN, L. V.;
ABDRAKHMANOV, I. B.; Russ. J. Org. Chem. 40 (2004) 12, 1764-1768; Inst. Org.
Chem., Ufa Res. Cent., Russ. Acad. Sci., Ufa 450054, Russia; Eng.) — R. Staver
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