A convenient method to construct (Z)-oxazines via 6-exo-dig iodocyclization and synthesis of indolin-3-one
Jaya Kishore Vandavasi1, Kung-Kai Kuo, Wan-Ping Hu
1Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung, Taiwan. jjwang@kmu.edu.tw.
Abstract:
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 (1)H 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.
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