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Synthesis of 1,3-diazaazulene derivatives of colchicinoids and isocolchicinoids via ipso- or tele-substitution-condensation with amidines

✍ Scribed by Marino Cavazza; Francesco Pietra

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 405 KB
Volume: 54
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(98)00856-4

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✦ Synopsis

Condensation of colchicinoids and isocolchicinoids with amidines in dry benzene affords regioselectively 1,3-diazaazulene derivatives: ipso-substitution-condensation products (e,g. 7) are best obtained from cycloheptatrienone-ring deactivated substrates (e.g. 4), whereas isomeric tele-subsfitution-condensation products (e.g. 13), are best accessible from cycloheptatrienone-ring activated subslrates (e.g. 10). Hydroxylic solvents inhibit tele-substitufion-condensation, arguably by undergoing protonation in preference of the intermediate o adduct.

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