Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 22, Pages 11351-11359Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01872
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- DST, New Delhi
- CSIR, New Delhi
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A transition-metal-free, K2S2O8-mediated intra-molecular, oxidative nitrogenation/oxygenation of C(sp(3))-H in N-aryl benzylic amines followed by oxidation at the benzylic center has been developed for the synthesis of benzamidine/benzoxazine heterocycles, providing an expedient access to quinazolin-4(3H)-ones, N-aryl-2-arylbenzimidazoles, and 4H-3,1-benzoxazin-4-ones. A considerable amount of work dealing with the mechanistic study to understand the crucial intramolecular cyclization step largely favors an iminium ion as the key intermediate.
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