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2005
Rearrangements
O 0140
A Versatile Aminobenzannulation Method Based on the Deprotonation of
and Similar 2-Aza-2,4-heptadienyl-6-ynes: A Multi05- 037 2-(1-Alkynyl)benzaldimines
step Rearrangement Cascade. — A new facile method for the aminobenzannulation
of aromatic and alicyclic β-halogenated enals is presented. Key step is the deprotonation of imines like (I) with LDA followed by trapping with various electrophiles (II).
The reaction mechanism is discussed in detail. Imines like (I) are generated by Sonogashira coupling of the starting β-halogenated enals with terminal alkynes and subsequent condensation with benzylamine (conditions not given). — (SAGAR, P.;
FROEHLICH, R.; WUERTHWEIN*, E.-U.; Angew. Chem., Int. Ed. 43 (2004) 42,
5694-5697; Org.-Chem. Inst., Westfael. Wilhelms Univ., D-48149 Muenster,
Germany; Eng.) — Mischke
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