Abstract
AbstractThe conversion of benzophenone methylhydrazone with bromine and pyridine into 1-[(methyldiazenyl)diphenylmethyl]pyridin-1-ium bromide followed by the solvolysis with methanol provides a facile synthesis of 1-(methoxydiphenylmethyl)-2-methyldiazene. The acid-induced hydrolysis of this N,O-ketal releases the methyldiazenyl moiety as the putative intermediate methyldiazenium ion. Reacting as a heterodienophile, methyldiazenium ion is intercepted with 1,3-dienes in [4 + 2+] cycloaddition reactions affording 1-methyl-1,2,3,6-tetrahydropyridazine Diels–Alder products which are transformed into stable and isolated N-benzoyl derivatives.
Graphical abstract
Funder
University of Innsbruck and Medical University of Innsbruck
Publisher
Springer Science and Business Media LLC
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