title: A convenient method to construct (Z)-oxazines via 6-exo-dig iodocyclization and synthesis of indolin-3-one.
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.
authors: Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung, Taiwan. jjwang@kmu.edu.tw.
authors: Jaya Kishore
authors: JK
authors: Vandavasi
authors: Kung-Kai
authors: KK
authors: Kuo
authors: Wan-Ping
authors: WP
authors: Hu
authors: Ho-Chanu
authors: HC
authors: Shen
authors: Wei-Sheng
authors: WS
authors: Lo
authors: Jeh-Jeng
authors: JJ
authors: Wang
mesh_terms: D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry; D011789:Quantum Theory
chemical_list: D007211:Indoles; D010078:Oxazines