Department of Chemistry, University of Cyprus , P.O. Box 20537, 1678 Nicosia, Cyprus.
J Org Chem. 2013 Oct 4;78(19):9906-13. doi: 10.1021/jo401648t. Epub 2013 Sep 20.
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.
2-氨基-N'-芳基脒与 4,5-二氯-1,2,3-二噻唑翁氯化物（Appel 盐）在 Hünig 碱（2 当量）的存在下反应，一步生成 3-芳基-4-亚氨基-3,4-二氢喹唑啉-2-甲腈，产率为 53-81%。提供了九个实例以及 4-亚氨基-3-苯基-3,4-二氢喹唑啉-2-甲腈的单晶 X 射线结构。此外，还研究了后者对酸和碱水解的行为。所有新化合物均经过充分表征，并提供了亚氨基喹唑啉形成的机理。
