An efficient synthesis of 2,4-disubstituted quinolines by electrophile-mediated cyclization reactions of 2-isocyanostyrene derivatives
An efficient synthesis of 2,4-disubstituted quinolines by electrophile-mediated cyclization reactions of 2-isocyanostyrene derivatives
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DOI：
10.1246/bcsj.77.553
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发表时间：
2004-03
影响因子：
4
通讯作者：
K. Kobayashi;Kenichi Takagoshi;S. Kondo;Osamu Morikawa;H. Konishi
中科院分区：
文献类型：
--
作者：
K. Kobayashi;Kenichi Takagoshi;S. Kondo;Osamu Morikawa;H. Konishi
介绍了一种以2-异氰基苯乙烯衍生物为原料合成喹啉的新方法。在催化量的乙醚-三氟化硼存在下，用醛（或丙酮）处理2-异氰基苯乙烯衍生物，得到在2-位带有1-羟烷基取代基的喹啉衍生物。以乙醛缩二乙醇或苯基环氧乙烷为亲电试剂，在相同条件下分别得到2-位带有1-乙氧基乙基或2-羟基-2-苯乙基取代基的喹啉衍生物。2-异氰基苯乙烯衍生物与N，N-二甲基异喹啉盐在无催化剂条件下反应，得到2-（1-二甲氨基烷基）喹啉。
A novel quinoline synthesis starting with 2-isocyanostyrene derivatives is described. The treatment of 2-isocyanostyrene derivatives with aldehydes (or acetone) in the presence of a catalytic amount of diethyl ether-borontrifluoride afforded quinoline derivatives carrying a 1-hydroxyalkyl substituent at the 2-position. The use of acetaldehyde diethyl acetal or phenyloxirane as an electrophile under the same conditions gave the corresponding quinoline derivatives, carrying the 1-ethoxyethyl or 2-hydroxy-2-phenylethyl substituent at the 2-position, respectively. 2-Isocyanostyrene derivatives reacted with N,N-dimethyliminium salts without any catalyst to give 2-(1-dimethylaminoalkyl)quinolines.