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Study of the lithiation of 3-substituted α-carbolines a new route to 3,4-disubstituted derivatives

✍ Scribed by Cyril Papamicaël; Georges Dupas; Jean Bourguignon; Guy Quéguiner

Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
329 KB
Volume
35
Category
Article
ISSN
0040-4039

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✦ Synopsis

The synthesis of new 3-substituted a-carbolines is described and these products were subjected to ortho-lithiation experiments. 3-pivalamido and 3-carboxamido derivatives are cleanly lithiated at 4position. The results are correlated with MNDO calculations. Various 3,4-disubstituted a-carbolines are obtained in excellent yields.

Our group has been interested for a long time in the metalation of x-deficient heterocycles. Good results were obtained in the pyridine and diazines series. 1 Nowadays, the association between metalation and cross-coupling reactions has become a powerful tool to obtain a large variety of natural producta We found interesting to study the metalation of tricyclic structures like a-carbolines because there is a lack of functionalization methods affording 2,3-or 3,4-disubstituted products in this series. Moreover, these

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