Acid-induced hydrolysis of 1-(methoxydiphenylmethyl)-2-methyldiazene: interception of methyldiazenium ion with 1,3-dienes affording 1-methyl-1,2,3,6-tetrahydropyridazine Diels–Alder products
نویسندگان
چکیده
Abstract The conversion of benzophenone methylhydrazone with bromine and pyridine into 1-[(methyldiazenyl)diphenylmethyl]pyridin-1-ium bromide followed by the solvolysis methanol provides a facile synthesis 1-(methoxydiphenylmethyl)-2-methyldiazene. acid-induced hydrolysis this N,O-ketal releases methyldiazenyl moiety as putative intermediate methyldiazenium ion. Reacting heterodienophile, ion is intercepted 1,3-dienes in [4 + 2 ] cycloaddition reactions affording 1-methyl-1,2,3,6-tetrahydropyridazine Diels–Alder products which are transformed stable isolated N -benzoyl derivatives. Graphical abstract
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ژورنال
عنوان ژورنال: Monatshefte Fur Chemie
سال: 2023
ISSN: ['1434-4475', '0026-9247']
DOI: https://doi.org/10.1007/s00706-023-03050-x