SYNTHESIS AND ANTIINFLAMMATORY ACTIVITY OF SOME 2,2-DIMETHYL-1,2-DIHYDROQUINOLINES
SYNTHESIS AND ANTIINFLAMMATORY ACTIVITY OF SOME 2,2-DIMETHYL-1,2-DIHYDROQUINOLINES
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DOI：
10.1021/jm00261a019
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发表时间：
1973-01-01
影响因子：
7.3
通讯作者：
BENSLAY, DN
中科院分区：
文献类型：
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作者：
DILLARD, RD;PAVEY, DE;BENSLAY, DN
以1，1-二甲基-2-丙基苯胺为原料合成了2，2-二甲基-L、2-二氢喹啉和4-氯-2，2-二甲基-1，2-二氢喹啉。这些化合物对紫外线诱导的豚鼠红斑有抑制作用。8-烷基衍生物是该系列化合物中最活跃的成员。Easton和Cassady报道了1，1-二甲基-2-丙基苯胺环合成1，2-二氢喹啉的报道。1我们研究了该环化反应，发现通过改变反应条件，还可以从该环化反应中分离出第二个产物4-氯-1，1-二甲基-1，2-二氢喹啉。与芳基1，1-二甲基-1-丙炔基醚的热重排不同，2苯胺重排是由亚铜盐催化的。因为这些组件-
The syntheses of 2, 2-dimethyl-l, 2-dihydroquinolines and 4-chloro-2, 2-dimethyl-1, 2-dihydroquinolines from 1, 1-dimethyl-2-propynylanilines are described. These compounds showed inhibition of uv-induced erythema in guinea pigs. The 8-alkyl derivatives were the most active members of the series.The intramolecular cyclization of 1, 1-dimethyl-2-propynylanilines to 1, 2-dihydroquinolines was reported by Easton and Cassady. 1We investigated this cyclization and found that a second product, 4-chloro-1, 1-dimethyl-1, 2-dihydroquinoline, also could be isolated from this cyclization by varying the reactionconditions. Unlike the thermal rearrangement of aryl 1, 1-dimethyl-1-propynyl ethers, 2 the aniline rearrangement was catalyzed by cuprous salts. Because these com-