Scandium Pentafluorobenzoate-Catalyzed Unexpected Cascade Reaction of 2-Aminobenzaldehydes with Primary Amines: A Process for the Preparation of Ring-Fused Aminals

作者：Mao, Dan; Tang, Jun; Wang, Wenbo; Wu, Shengying; Liu, Xin; Yu, Jianjun^*; Wang, Limin

来源：Journal of Organic Chemistry, 2013, 78(24): 12848-12854.

DOI：10.1021/jo402331t

• ONE-POT SYNTHESIS
• YTTERBIUM PERFLUOROOCTANOATE
• ACID-DERIVATIVES
• ALPHA-AMINATION
• NITROGEN
• CHEMISTRY
• CYCLIZATIONS
• HETEROCYCLES
• QUINOLINES
• EFFICIENT

An unexpected cascade reaction of 2-aminobenzaldehydes with arylamines catalyzed by scandium pentafluorobenzoate [Sc(Pfb)(3)] was reported as a facile strategy for the efficient synthesis of a novel class of polycyclic ring-fused aminals N-substituted-6,7,11b,13-tetrahydro-6,12-[1,2]benzenoquinazolino[3,4-a]-quinazolin-13-amines 1. Under similar conditions, a series of the analogues of Troger's base, 13-substituted-5,6,11,12-tetrahydro-6,12-epiminodibenzo[b,f][1,5]diazocines 2 were obtained when the arylamines were replaced by methanamines. A possible mechanism for the formation of 1 and 2 was proposed.

• 出版日期2013-12-20
• 单位华东理工大学