1456546-90-9Relevant academic research and scientific papers
A convenient method to construct (Z)-oxazines via 6-exo-dig iodocyclization and synthesis of indolin-3-one
Vandavasi, Jaya Kishore,Kuo, Kung-Kai,Hu, Wan-Ping,Shen, Ho-Chanu,Lo, Wei-Sheng,Wang, Jeh-Jeng
, p. 6520 - 6525 (2013/09/24)
An efficient regio-, stereo- and chemo-specific synthesis of 1,3-benzoxazines via 6-exo-dig cyclization to afford the Z-isomer is reported. The structure and connectivity were confirmed unambiguously on the basis of 1H NMR, NOESY, and ORTEP. Furthermore, DFT studies revealed that the Z-isomer was more stable than the E-isomer. Iodine substituted 1,3-benzoxazines were very useful precursors for cross coupling reactions. Suzuki reaction was carried out successfully and the resulting product was transformed to 1-(4-nitrobenzoyl)-2,2-diphenylindolin-3-one in the presence of a Lewis acid.
