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Transformation of 2-methyl-1-phenylethynyl-1,2,3,4-tetrahydroisoquinoline by the action of activated alkynes
Chemistry of Heterocyclic Compounds ( IF 1.4 ) Pub Date : 2018-06-29 , DOI: 10.1007/s10593-018-2306-y
Leonid G. Voskressensky , Reza Samavati , Alexander А. Titov , Elena V. Alexandrova , Natalia Yu. Chernikova , Alexey V. Varlamov

Transformations of 2-methyl-1-phenylethynyl-1,2,3,4-tetrahydroisoquinoline resulting from the action of activated alkynes in trifluoroethanol and hexafluoroisopropanol were studied. In reactions with dimethyl acetylenedicarboxylate, 6-phenylethynyl-substituted benzazocines were prepared, while methyl 4-benzyl-5-(2-ethenylphenyl)-1-methyl-1H-pyrrole-3-carboxylate and benzo[d][3]-azacyclodeca[4,6,7]triene with the allene fragment, respectively, were isolated in reactions with methyl propiolate and acetylacetylene in addition to the corresponding benzazocines. As a rule, in hexafluoroisopropanol, the yields of azocines are higher. In reaction with acetylacetylene in dichloromethane, 1-(2-acetylvinyl)-1-phenylethynyltetrahydroisoquinoline is formed in high yield.


中文翻译:

活化炔烃的作用转化2-甲基-1-苯基乙炔基-1,2,3,4-四氢异喹啉

研究了活化炔烃在三氟乙醇和六氟异丙醇中产生的2-甲基-1-苯基乙炔基-1,2,3,4-四氢异喹啉的转化。在与乙炔二羧酸二甲酯的反应中,制备了6-苯基乙炔基取代的苯并恶唑啉,而4-苄基-5-(2-乙烯基苯基)-1-甲基-1 H-吡咯-3-羧酸甲酯和苯并[ d ] [3]-分别与丙二酸甲酯和乙酰基乙炔反应分离的苯并偶氮恶唑中,分别分离出具有丙二烯片段的氮杂环十[4,6,7]三烯。通常,在六氟异丙醇中,偶氮素的产率较高。通过与乙酰乙炔在二氯甲烷中反应,可以高产率形成1-(2-乙酰乙烯基)-1-苯基乙炔基四氢异喹啉。
更新日期:2018-06-29
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