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机构地区:[1]兰州大学功能有机分子化学国家重点实验室,兰州730000
出 处:《高等学校化学学报》2007年第10期1881-1884,共4页Chemical Journal of Chinese Universities
基 金:国家自然科学基金(批准号:20472027)资助.
摘 要:以BF3.OEt2为催化剂,在室温下通过4-羟基-N-苯基[1,3]苯并噁嗪-2-酮的脱羟基产生N-苯基[1,3]苯并噁嗪正离子,然后与富电子烯烃发生Diels-Alder反应,合成出了一系列喹啉并[1,2-c1,3]苯并噁嗪-6-酮和喹啉并[1,2-c1,3]萘并噁嗪-6-酮衍生物.The N-acyliminium cations are powerful intermediates in the construction of nitrogen-containing heterocycles. They are much more reactive than iminium cations in both intramolecular cyclizations and intermolecular cycloadditions. In this paper, a new and efficient route for the synthesis of quino [ 1,2-c ] [ 1,3 ] benzoxazin-6-ones (3a-3h) and quino [ 1,2-c ] [ 1,3 ] naphthoxazin-6-ones (3i-3j) was developed via Diels- Alder reaction of N-acyliminium cations with olefins (2a-2d) in moderate and good yields at an ambient temperature. The N-acyliminium cations, N-phenyl [ 1,3 ] benzoxazin-2-onium ion and N-phenyl [ 1,3 ] naphthoxazin-2-onium ion, are easily prepared by BF3 ·OEt2 catalyzed dehydroxylation of 4-hydroxy-3-phenyl [ 1,3 ] benzoxazin-2-ones ( 1 a-1 c ) and 4-hydroxy-3-phenyl [ 1,3 ] naphthoxazin-2-one ( 1 d ).
关 键 词:喹啉并[1 2-c][1 3]苯并噁嗪-6-酮 4-羟基-N-苯基[1 3]苯并噁嗪-2-酮 N-酰基亚铵离子
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