Generation of N-H Imines from α-Azidocarboxylic Acids through Ru-Catalyzed Decarboxylation
Hwi Yul Jo1, Jeong Min Lee1, Ewa Pietrasiak1
1Department of Chemistry, POSTECH, (Pohang University of Science and Technology), Pohang 37673, Republic of Korea.
Abstract:
A new method for the synthesis of N-H imines from α-azidocarboxylic acids was developed, which proceeds through decarboxylative C-C bond cleavage catalyzed by a commercial diruthenium complex ([CpRu(CO)2]2) under visible light irradiation at room temperature within several minutes. The reactive products undergo condensation, which forms cyclic trimers (2,4,6-trialkylhexahydro-1,3,5-triazines) or linear N,N'-bis(arylmethylidene)arylmethanediamines in quantitative yields. Alternatively, the N-H imines can be trapped with benzylamine and 2-(aminomethyl)aniline, providing stable N-benylimines and tetrahydroquinazolines, respectively. Subsequent oxidation of tetrahydroquinazolines produced quinazolines.
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