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Solid-phase synthesis of substituted cinnolines by a Richter type cleavage protocol

✍ Scribed by Stefan Bräse; Stefan Dahmen; Jean Heuts

Book ID
104261949
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
146 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

Starting from triazene bound ortho-halo arenes on a solid support, palladium-catalyzed alkynylations and subsequent cleavage reactions under acidic conditions give rise to ortho-alkynylaryldiazonium salts, which in turn undergo cyclization to afford substituted 4-halo-and 4-hydroxycinnolines in moderate to good yields. The method is applicable to automated synthesis.

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