STUDIES IN THE CYANINE DYE SERIES .11. THE MEROCYANINES
STUDIES IN THE CYANINE DYE SERIES .11. THE MEROCYANINES
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DOI：
10.1021/ja01155a095
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发表时间：
1951-01-01
影响因子：
15
通讯作者：
WHITE, FL
中科院分区：
文献类型：
--
作者：
BROOKER, LGS;KEYES, GH;WHITE, FL
非环酮亚甲基化合物包括以下化合物：乙酰丙酮、丙二酸乙酯、丙二酸乙酯、氰乙酰胺、氰乙酰苯胺、氰基苯乙酮、氰乙酸乙酯。因此，2-甲硫基苯并噻唑甲氧基对甲苯磺酸与乙酰丙酮缩合得到VII，这是一种在进一步反应中有用的开链花菁(参看。XII)。2-甲硫基苯并噻唑反应的缩合产物对于含有反应性烷基-硫醇或类似负基的杂环碱的季盐转化为含有反应性甲基的盐有价值，而后者是以其他方式无法获得的。5含酰胺类发色团含氮的环，除上述苯并噻唑、2-和4-吡啶和喹啉环外，还包括噻唑啉、噻唑、吡咯等单环体系；苯并恶唑、苯并噻唑、1-异喹啉、拟吲哚、苯并咪唑等缩合双环体系；苯并喹啉、萘并恶唑和萘并噻唑等缩合三环体系。这一系列的第一个代表是由Rodd和Watts制备的，6他们用含有/3-苯胺基(或乙酰苯胺基)-乙烯基的中间体7处理含有反应性亚甲基的吡唑酮类化合物7，例如2-/J-ACET-苯胺基苯并噻唑乙碘(X，
Non-cychc keto-methylene compounds include the following: acetylacetone, ethyl malonate, malonanilide, cyanoacetamide, cyanoacetanilide, cyanoacetophenone, ethyl cyanoacetate. Thus, condensation of 2-methylmercaptobenzothiazole metho-p-toluenesulfonate with acetylacetone gives VII, an open-chain merocyanine that is useful in further reactions (cf. XII). The condensation product of the 2-methylmercaptobenzothiazolium reaction is of value for theconversion of quaternary salts of heterocyclic bases containing reactive alkyl-mercapto, or similar negative groups, into salts containing reactive methyl, when these latter are not otherwise accessible. 5 The rings which contain the nitrogen of the amidic chromophore include, besides the benzothiazole and the 2-and 4-pyridine and quinoline rings already mentioned, single-ring systems such as thiazoline, thiazole and pyrrole; condensed two-ring systems such as benzoxazole, benzoselenazole, 1-isoquinoline, pseudo-indole, benzimidazole; condensed three-ring systems such as the benzoquinolines and the naphthoxazoles and naphthothiazoles.The next highervinylogs of the simple mero-cyanines, such as III (= 1) may be called “merocarbocyanines.” The first representatives of this series were prepared by Rodd and Watts, 6 who treated pyrazolones containing a reactive methylene group with intermediates containing the/3-anilino (or acetanilido)-vinyl group, 7 such as 2-/J-acet-anilidovinylbenzothiazole ethiodide (X,