One-Step Conversion of 2‑Amino‑N′‑arylbenzamidines into 3‑Aryl-4-imino-3,4-dihydroquinazoline-2-carbonitriles
Using 4,5-Dichloro-1,2,3-dithiazolium Chloride
posted on 2015-12-16, 23:40authored byStyliana
I. Mirallai, Manolis J. Manos, Panayiotis A. Koutentis
2-Amino-N′-arylbenzamidines
react with
4,5-dichloro-1,2,3-dithiazolium chloride (Appel salt) in the presence
of Hünig’s base (2 equiv) to give in one step 3-aryl-4-imino-3,4-dihydroquinazoline-2-carbonitriles
in 53–81% yields. Nine examples are presented along with the
single-crystal X-ray structure of 4-imino-3-phenyl-3,4-dihydroquinazoline-2-carbonitrile.
Furthermore, the behavior of the latter toward both acid and base
hydrolysis is investigated. All new compounds are fully characterized,
and a mechanistic rationale for the formation of the iminoquinazolines
is provided.