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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

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Figshare2015-12-16 更新2026-04-29 收录
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https://figshare.com/articles/dataset/One_Step_Conversion_of_2_Amino_i_N_i_arylbenzamidines_into_3_Aryl_4_imino_3_4_dihydroquinazoline_2_carbonitriles_Using_4_5_Dichloro_1_2_3_dithiazolium_Chloride/2026068
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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.
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2015-12-16
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