文章基本信息

标题：A Synthesis of 1, 2-Tetramethylene-3, 4-dihydro-β-carboline
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作者：Shigehiko Sugasawa ; Masanao Terashima ; Yuichi Kanaoka 等
期刊名称：Chemical and Pharmaceutical Bulletin
印刷版ISSN：0009-2363
电子版ISSN：1347-5223
出版年度：1956
卷号：4
期号：1
页码：16-19
DOI：10.1248/cpb1953.4.16
出版社：The Pharmaceutical Society of Japan
摘要：3, 4-Dihydro-1, 2-tetramethylene-β-carboline (I) was synthesized from 2-(2'-pyridyl) indole by a new method.The latter, when treated with fromaldehyde and diethylamine, readily geve the β-diethylaminomethyl derivative (III) in a fair yield. Its methiodide (V), made advantageously via the corresponding methosulfate (IV), was reacted with aqueous alkali cyanide to give the indolylacetonitrile (VI), which was hydrolysed and esterified, giving the indolylacetic ester (VIII). LiAlH₄-reduction of this ester yielded the β-hydroxyethyl derivative (IX), which gave directly the β-carbolinium bromide (X) by the agency of PBr₃, catalytic reduction of which gave (I) in a smooth reaction. The hitherto unknown 2-(3'-pyridyl)-and 2-(4'-pyridyl)-indoles, their metho-salts and the corresponding 2-piperidyl indoles were also prepared.