New nucleophilic rearrangement in the mechanism of the three-component domino cyclisation affording fluoroalkylated (pyrrolo)quinazolines

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• 作者：Old艡ich Paleta ; Bohumil Dolensk媒 ; Ji艡铆 Pale膷ek ; Jaroslav Kv铆膷ala
• 关键词：Three-component cyclisation ; Mechanism ; Substituted pyrroloquinazolines ; Trifluoropyruvate aldols ; Enamine nucleophiles ; Nucleophilic rearrangement
• 刊名：Journal of Fluorine Chemistry
• 出版年：January, 2014
• 年：2014
• 卷：157
• 期：Complete
• 页码：1-11
• 全文大小：1229 K

文摘

The following mechanism steps were verified for the three-component domino cyclisation affording (pyrrolo)quinazolines from 2-(aminomethyl)aniline, a very reactive oxo compound and 鈥渦sual鈥?oxo compound. The first step was a rapid reaction of very reactive oxo compound (trifluoropyruvate or hexafluoroacetone) with benzylic amino group to form hemiaminal, but not imine; the second step was the reaction of oxo compound with aromatic amino group to form imine (Schiff base) being in equilibrium with its enamine form; the third step was an intramolecular attack of the hemiaminal carbon by the enamine carbon followed by a new nucleophilic rearrangement to form tetrahydropyrimidine cycle; the forth step was closure of the lactam ring, if ester group was available as in trifluoropyruvate.